Synthesis routes of Raltegravir potassium

Raltegravir potassium

Numéro de catalogue B1684573

: 871038-72-1

Poids moléculaire: 482.5 g/mol

Clé InChI: IFUKBHBISRAZTF-UHFFFAOYSA-M

Attention: Uniquement pour un usage de recherche. Non destiné à un usage humain ou vétérinaire.

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Patent

US08722722B2

Procedure details

A solution of Raltegravir potassium (˜2 g) in water was acidified with 2N HCl until pH 2 was obtained. The acidified solution was extracted with MTBE (600 ml). The organic extract was evaporated to dryness. Raltegravir free hydroxy (1.5 g) was obtained as a white powder.

Name

Raltegravir potassium

Quantity

2 g

Type

reactant

Reaction Step One

Name

HCl

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

water

Quantity

0 (± 1) mol

Type

solvent

Reaction Step Three

Name

Raltegravir

Identifiers

REACTION_CXSMILES

[CH3:1][C:2]1[O:6][C:5]([C:7]([NH:9][C:10]([C:13]2[N:19]([CH3:20])[C:17](=[O:18])[C:16]([O-:21])=[C:15]([C:22]([NH:24][CH2:25][C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)=[O:23])[N:14]=2)([CH3:12])[CH3:11])=[O:8])=[N:4][N:3]=1.[K+].Cl>O>[CH3:1][C:2]1[O:6][C:5]([C:7]([NH:9][C:10]([C:13]2[N:19]([CH3:20])[C:17](=[O:18])[C:16]([OH:21])=[C:15]([C:22]([NH:24][CH2:25][C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)=[O:23])[N:14]=2)([CH3:12])[CH3:11])=[O:8])=[N:4][N:3]=1 |f:0.1|

Inputs

Step One

Name	Raltegravir potassium
Quantity	2 g
Type	reactant
Smiles	CC1=NN=C(O1)C(=O)NC(C)(C)C2=NC(=C(C(=O)N2C)[O-])C(=O)NCC=3C=CC(=CC3)F.[K+]

Step Two

Name	HCl
Quantity	0 (± 1) mol
Type	reactant
Smiles	Cl

Step Three

Name	water
Quantity	0 (± 1) mol
Type	solvent
Smiles	O

Conditions

Other

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

Workups

CUSTOM

Type	CUSTOM
Details	was obtained

EXTRACTION

Type	EXTRACTION
Details	The acidified solution was extracted with MTBE (600 ml)

EXTRACTION

Type	EXTRACTION
Details	The organic extract

CUSTOM

Type	CUSTOM
Details	was evaporated to dryness

Outcomes

Product

Name	Raltegravir
Type	product
Smiles	CC1=NN=C(O1)C(=O)NC(C)(C)C2=NC(=C(C(=O)N2C)O)C(=O)NCC=3C=CC(=CC3)F

Measurements

Type	Value	Analysis
AMOUNT: MASS	1.5 g
YIELD: CALCULATEDPERCENTYIELD	81.4%

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.