Sodium borohydride → HCID 89525739, compound

HRID 2278359Notes

Reaction equation

HRID 2278359 reaction equation
[Si:1]([O:8][CH2:9][CH:10]([N:24]([CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37])[S:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:27])=[O:26])[C:11]1[S:12][CH:13]=[C:14]([CH:16]=[N:17][S:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])[CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[Si:1]([O:8][CH2:9][CH:10]([N:24]([CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37])[S:25]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)(=[O:26])=[O:27])[C:11]1[S:12][CH:13]=[C:14]([CH2:16][NH:17][S:18]([C:20]([CH3:22])([CH3:23])[CH3:21])=[O:19])[CH:15]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 131733453HCID 131733453, compound

Product 1

HCID 89525739HCID 89525739, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[2-{[tert-butyl(dimethyl)silyl]oxy}-1-(4-{[(tert-butylsulfinyl)imino]methyl}thiophen-2-yl)ethyl]-N-(3-methylbutyl)benzenesulfonamide (146 mg, 0.244 mmol) was dissolved in 2.4 mL MeOH at −78° C. Sodium borohydride (11.99 mg, 0.317 mmol) was added and the mixture was then warmed to room temperature and stirred for 1 hour. The reaction was quenched slowly with saturated NaHCO3, after which DCM was added and the phases separated with a phase extractor. The DCM was removed under reduced pressure.

Workup

  1. customThe reaction was quenched slowly with saturated NaHCO3
  2. additionafter which DCM was added
  3. customthe phases separated with a phase extractor
  4. customThe DCM was removed under reduced pressure

Sources & evidence

ORD record
ord-e3332140999341dd9ba6f8f6aed69367
Source dataset
uspto-grants-2015_09
Patent number
US09133157B2

Reaction notes

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