Sodium borohydride → HCID 20740212, compound

HRID 1883138Notes

Reaction equation

HRID 1883138 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][C@@H:6]([C:29]#[N:30])[NH:7][C:8]([C@@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]1[NH:16][C:17]([C:19]1[N:20]([CH3:28])[C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[O:9].[BH4-].[Na+]>CO.C(Cl)Cl>[C:29]([CH:6]([NH:7][C:8]([C@@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]1[NH:16][C:17]([C:19]1[N:20]([CH3:28])[C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[O:9])[CH2:5][CH2:4][CH2:3][OH:2])#[N:30]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 60083628HCID 60083628, compound2×

Product 1

HCID 20740212HCID 20740212, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-4-cyano-4-({(1R,2S)2-[(1-methyl-1H-indole-2-carbonyl)-amino]-cyclohexanecarbonyl}-amino)-butyric acid methyl ester (obtained from compound 3-8, 209 mg, 0.492 mmol), in 15 mL of MeOH and 15 mL of CH2Cl2, was added sodium borohydride (100 mg, 2.64 mmol). The reaction mixture was stirred at ambient temperature for 24 hours, concentrated, and purified by column chromatography (3:97, MeOH/CH2Cl2) to give 83 mg (43%) of 1-methyl-1H-indole-2-carboxylic acid [(1S,2R)-2-(1-cyano-4-hydroxy-butylcarbamoyl)-cyclohexyl]-amide as an amorphous solid. MS: 397 (M+H+).

Workup

  1. concentrationconcentrated
  2. custompurified by column chromatography (3:97, MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-f32c8c7ba00148bb8e1e238bcfef9d01
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

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