Sodium borohydride → {(2R,3S)-4-(3,5-difluoro-phenyl)-3-[3-(1,1-dioxo-1lambda6-[1,2]thiazinan-2-yl)-5-(1-hydroxy-ethyl)-benzoylamino]-2-hydroxy-butyl}-(3-methoxy-benzyl)-carbamic acid tert-butyl ester

HRID 1454203Notes

Reaction equation

HRID 1454203 reaction equation
[C:1]([O:5][C:6](=[O:50])[N:7]([CH2:17][C@@H:18]([OH:49])[C@@H:19]([NH:29][C:30](=[O:48])[C:31]1[CH:36]=[C:35]([N:37]2[CH2:42][CH2:41][CH2:40][CH2:39][S:38]2(=[O:44])=[O:43])[CH:34]=[C:33]([C:45](=[O:47])[CH3:46])[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:50])[N:7]([CH2:17][C@@H:18]([OH:49])[C@@H:19]([NH:29][C:30](=[O:48])[C:31]1[CH:32]=[C:33]([CH:45]([OH:47])[CH3:46])[CH:34]=[C:35]([N:37]2[CH2:42][CH2:41][CH2:40][CH2:39][S:38]2(=[O:43])=[O:44])[CH:36]=1)[CH2:20][C:21]1[CH:22]=[C:23]([F:28])[CH:24]=[C:25]([F:27])[CH:26]=1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57529282[(2R,3S)-3-[3-acetyl-5-(1,1-dioxo-1lambda6-[1,2]thiazinan-2-yl)-benzoylamino]-4-(3,5-difluoro-phenyl)-2-hydroxy-butyl]-(3-methoxy-benzyl)-carbamic acid tert-butyl ester

Product 1

HCID 57529323{(2R,3S)-4-(3,5-difluoro-phenyl)-3-[3-(1,1-dioxo-1lambda6-[1,2]thiazinan-2-yl)-5-(1-hydroxy-ethyl)-benzoylamino]-2-hydroxy-butyl}-(3-methoxy-benzyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[(2R,3S)-3-[3-Acetyl-5-(1,1-dioxo-1λ6-[1,2]thiazinan-2-yl)-benzoylamino]-4-(3,5-difluoro-phenyl)-2-hydroxy-butyl]-(3-methoxy-benzyl)-carbamic acid tert-butyl ester (16 mg, 0.022 mmol) was dissolved in MeOH (0.2 mL) and sodium borohydride (1.13 mg, 0.03 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 to give the title compound which was used in the next step without further purification: HPLC retention time: 2.073 min (method A). MS (ESI) (M+H)+ 718.30.

Workup

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

Sources & evidence

ORD record
ord-d129e75359fd4363ae549803a9ac05b9
Source dataset
uspto-grants-2009_01
Patent number
US07476764B2

Reaction notes

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