Sodium borohydride → {(2R,3S)-4-(3,5-Difluoro-phenyl)-3-[3-[1-(4-fluoro-phenyl)-ethylcarbamoyl]-5-(1-hydroxy-ethyl)-benzoylamino]-2-hydroxy-butyl}-(3-methoxy-benzyl)-carbamic acid tert-butyl ester

HRID 1454213Notes

Reaction equation

HRID 1454213 reaction equation
[C:1]([O:5][C:6](=[O:54])[N:7]([CH2:17][C@@H:18]([OH:53])[C@@H:19]([NH:29][C:30](=[O:52])[C:31]1[CH:36]=[C:35]([C:37](=[O:48])[NH:38][CH:39]([C:41]2[CH:46]=[CH:45][C:44]([F:47])=[CH:43][CH:42]=2)[CH3:40])[CH:34]=[C:33]([C:49](=[O:51])[CH3:50])[CH:32]=1)[CH2:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[CH:22]=1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([O:5][C:6](=[O:54])[N:7]([CH2:17][C@@H:18]([OH:53])[C@@H:19]([NH:29][C:30](=[O:52])[C:31]1[CH:32]=[C:33]([CH:49]([OH:51])[CH3:50])[CH:34]=[C:35]([C:37](=[O:48])[NH:38][CH:39]([C:41]2[CH:42]=[CH:43][C:44]([F:47])=[CH:45][CH:46]=2)[CH3:40])[CH:36]=1)[CH2:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[CH:22]=1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57529278[(2R,3S)-3-{3-Acetyl-5-[1-(4-fluoro-phenyl)-ethylcarbamoyl]-benzoyl-amino}-4-(3,5-difluoro-phenyl)-2-hydroxy-butyl]-(3-methoxy-benzyl)-carbamic acid tert-butyl ester

Product 1

HCID 68827840{(2R,3S)-4-(3,5-Difluoro-phenyl)-3-[3-[1-(4-fluoro-phenyl)-ethylcarbamoyl]-5-(1-hydroxy-ethyl)-benzoylamino]-2-hydroxy-butyl}-(3-methoxy-benzyl)-carbamic acid tert-butyl esterYield 99.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[(2R,3S)-3-{3-Acetyl-5-[1-(4-fluoro-phenyl)-ethylcarbamoyl]-benzoyl-amino}-4-(3,5-difluoro-phenyl)-2-hydroxy-butyl]-(3-methoxy-benzyl)-carbamic acid tert-butyl ester (10 mg, 0.0134 mmol) was dissolved in MeOH (0.1 mL) and sodium borohydride (0.68 mg, 0.0179 mmol) was added. The reaction mixture was stirred at room temperature for 2 h. The mixture was concentrated and partitioned between ethyl acetate and H2O. The organic layer was separated and concentrated under vacuum to give the title compound (10 mg): HPLC retention time: 2.243 min (method A). MS (ESI) (M+H)+ 750.40.

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between ethyl acetate and H2O
  3. customThe organic layer was separated
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6e73c854032546958f334b88a2b4e04a
Source dataset
uspto-grants-2009_01
Patent number
US07476764B2

Reaction notes

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