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molecular formula C5H9ClO3 B076961 Methyl 4-chloro-3-hydroxybutanoate CAS No. 10488-68-3

Methyl 4-chloro-3-hydroxybutanoate

Katalognummer B076961
Molekulargewicht: 152.57 g/mol
InChI-Schlüssel: WMRINGSAVOPXTE-UHFFFAOYSA-N
Achtung: Nur für Forschungszwecke. Nicht für den menschlichen oder tierärztlichen Gebrauch.
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Patent
US04686296

Procedure details

In 10 ml of ethanol, 1.11 g (10 m.moles) of glycinamide hydrochloride, 1.06 g (10 m.moles) of sodium carbonate, and 1.53 g (10 m.moles) of methyl 4-chloro-3-hydroxybutyrate were stirred and refluxed simultaneously for 20 hours. After completion of the reaction, the warm reaction mixture was filtered to expel inorganic salts. The filtrate was analyzed by gas chromatography (Fluoxylate-K 1% Uniport HP 100/120, column length 0.5 m and column temperature 220° C., RT 2.8 min) (hereinafter referred to as "GC" for short). Consequently, the reaction was found to have produced oxiracetam in a yield of 75%. The filtrate was concentrated, dissolved in a small amount of water, and poured on a bed of 40 ml of Amberlite IR-120 (--SO3H form) (tradename: Rohm & Haas Co.). The adsorbate was eluted with water. The eluate was fractionated, with the first and second fractions discarded and the third and following fractions were collected. The collected fractions were concentrated. The concentrate was dissolved in methanol and the solution was ice cooled ad crystallized with crystals of oxiracetam used as mother crystals. The produced crystals were collected and vaccum dried, to afford 0.55 g (yield of isolation 35%) of oxiracetam, having a melting point of 155° to 160° C. (as compared with 161° to 163° C. reported in the specification of Japanese Patent Publication Sho 58-22,034/1983).
Name
glycinamide hydrochloride
Quantity
1.11 g
Type
reactant
Reaction Step One
Quantity
1.06 g
Type
reactant
Reaction Step One
Quantity
1.53 g
Type
reactant
Reaction Step One
Quantity
10 mL
Type
solvent
Reaction Step One
Yield
75%

Identifiers

REACTION_CXSMILES
Cl.[NH2:2][CH2:3][C:4]([NH2:6])=[O:5].C(=O)([O-])[O-].[Na+].[Na+].Cl[CH2:14][CH:15]([OH:21])[CH2:16][C:17](OC)=[O:18]>C(O)C>[CH2:16]1[C:17](=[O:18])[N:2]([CH2:3][C:4]([NH2:6])=[O:5])[CH2:14][CH:15]1[OH:21] |f:0.1,2.3.4|

Inputs

Step One
Name
glycinamide hydrochloride
Quantity
1.11 g
Type
reactant
Smiles
Cl.NCC(=O)N
Name
Quantity
1.06 g
Type
reactant
Smiles
C([O-])([O-])=O.[Na+].[Na+]
Name
Quantity
1.53 g
Type
reactant
Smiles
ClCC(CC(=O)OC)O
Name
Quantity
10 mL
Type
solvent
Smiles
C(C)O

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
refluxed simultaneously for 20 hours
Duration
20 h
CUSTOM
Type
CUSTOM
Details
After completion of the reaction
CUSTOM
Type
CUSTOM
Details
the warm reaction mixture
FILTRATION
Type
FILTRATION
Details
was filtered
CUSTOM
Type
CUSTOM
Details
was analyzed by gas chromatography (Fluoxylate-K 1% Uniport HP 100/120, column length 0.5 m and column temperature 220° C., RT 2.8 min)
Duration
2.8 min

Outcomes

Product
Name
Type
product
Smiles
C1C(CN(C1=O)CC(=O)N)O
Measurements
Type Value Analysis
YIELD: PERCENTYIELD 75%

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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