Synthesis routes of Fingolimod

Fingolimod

カタログ番号 B1672674

: 162359-55-9

分子量: 307.5 g/mol

InChIキー: KKGQTZUTZRNORY-UHFFFAOYSA-N

注意: 研究専用です。人間または獣医用ではありません。

在庫あり

専門家チームからの見積もりを受け取るには、QUICK INQUIRYをクリックしてください。
品質商品を競争力のある価格で提供し、研究に集中できます。

Patent

US05952316

Procedure details

A suspension of sodium borohydride (0.60 g) and lithium bromide (1.66 g) in ethanol (17 ml) was stirred at room temperature for 25 minutes. Ethyl 2-amino-2-ethoxycarbonyl-4-(4-octylphenyl)butyrate (1.24 g) was dropwise added thereto over 3 minutes and the mixture was stirred at room temperature for 5 hours. Water (40 ml) was added to the reaction mixture and the mixture was stirred for 40 minutes. The crystals precipitated was collected by filtration and dried to give 0.68 g of the subject compound, melting point=125-126° C. Treatment of the subject compound with hydrochloric acid-ethanol gives the corresponding hydrochloride.

Name

sodium borohydride

Quantity

0.6 g

Type

reactant

Reaction Step One

Name

lithium bromide

Quantity

1.66 g

Type

reactant

Reaction Step One

Name

ethanol

Quantity

17 mL

Type

solvent

Reaction Step One

Name

Ethyl 2-amino-2-ethoxycarbonyl-4-(4-octylphenyl)butyrate

Quantity

1.24 g

Type

reactant

Reaction Step Two

Name

Water

Quantity

40 mL

Type

reactant

Reaction Step Three

Name

subject compound

Identifiers

REACTION_CXSMILES

[BH4-].[Na+].[Br-].[Li+].[NH2:5][C:6]([C:28](OCC)=[O:29])([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:16][CH:15]=1)[C:7](OCC)=[O:8].O>C(O)C>[NH2:5][C:6]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:16][CH:15]=1)([CH2:28][OH:29])[CH2:7][OH:8] |f:0.1,2.3|

Inputs

Step One

Name	sodium borohydride
Quantity	0.6 g
Type	reactant
Smiles	[BH4-].[Na+]

Name	lithium bromide
Quantity	1.66 g
Type	reactant
Smiles	[Br-].[Li+]

Name	ethanol
Quantity	17 mL
Type	solvent
Smiles	C(C)O

Step Two

Name	Ethyl 2-amino-2-ethoxycarbonyl-4-(4-octylphenyl)butyrate
Quantity	1.24 g
Type	reactant
Smiles	NC(C(=O)OCC)(CCC1=CC=C(C=C1)CCCCCCCC)C(=O)OCC

Step Three

Name	Water
Quantity	40 mL
Type	reactant
Smiles	O

Conditions

Temperature

Control Type

AMBIENT

Stirring

Type	CUSTOM
Details	was stirred at room temperature for 25 minutes
Rate	UNSPECIFIED
RPM	0

Other

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

Workups

WAIT

Type	WAIT
Details	over 3 minutes
Duration	3 min

STIRRING

Type	STIRRING
Details	the mixture was stirred at room temperature for 5 hours
Duration	5 h

STIRRING

Type	STIRRING
Details	the mixture was stirred for 40 minutes
Duration	40 min

CUSTOM

Type	CUSTOM
Details	The crystals precipitated

FILTRATION

Type	FILTRATION
Details	was collected by filtration

CUSTOM

Type	CUSTOM
Details	dried

Outcomes

Product

Details

Reaction Time

25 min

Name	subject compound
Type	product
Smiles	NC(CO)(CO)CCC1=CC=C(C=C1)CCCCCCCC

Measurements

Type	Value	Analysis
AMOUNT: MASS	0.68 g
YIELD: CALCULATEDPERCENTYIELD	69.8%

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.