Sodium borohydride → HCID 11979128, compound

HRID 1162708Notes

Reaction equation

HRID 1162708 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])[CH:5]=[CH:4][C:3]=1[NH:15][C:16]([N:18]1[CH2:22][C:21](=[O:23])[C@H:20]([CH2:24][NH:25][C:26]([C:28]2[S:29][C:30]([Cl:33])=[CH:31][CH:32]=2)=[O:27])[CH2:19]1)=[O:17].[BH4-].[Na+]>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])[CH:5]=[CH:4][C:3]=1[NH:15][C:16]([N:18]1[CH2:22][C@H:21]([OH:23])[C@H:20]([CH2:24][NH:25][C:26]([C:28]2[S:29][C:30]([Cl:33])=[CH:31][CH:32]=2)=[O:27])[CH2:19]1)=[O:17]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58748171HCID 58748171, compound

Product 1

HCID 11979128HCID 11979128, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-3-{[(5-chloro-thiophene-2-carbonyl)-amino]-methyl}-4-oxo-pyrrolidine-1-carboxylic acid[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenyl]-amide (example 81.3; 50 mg) in 2 ml of THF was added at 22° C. 12 mg of NaBH4 and stirring was continued for 1.5 h. The mixture was partitioned between 1 N HCl and AcOEt, the organic layer was washed with brine, dried and evaporated to give (3R,4R)-3-{[(5-chloro-thiophene-2-carbonyl)-amino]-methyl}-4-hydroxy-pyrrolidine-1-carboxylic acid[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenyl]-amide. White solid. MS491.3 ([M+H]+)

Workup

  1. customThe mixture was partitioned between 1 N HCl and AcOEt
  2. washthe organic layer was washed with brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-7e127b613909493eb5319d3b79fd890d
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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