Sodium borohydride → HCID 131733467, compound

HRID 2278378Notes

Reaction equation

HRID 2278378 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([N:24]([CH2:37][CH:38]([CH3:40])[CH3:39])[S:25]([C:28]1[CH:36]=[CH:35][C:31]2[N:32]=[CH:33][S:34][C:30]=2[CH:29]=1)(=[O:27])=[O:26])[C:11]1[S:12][C:13](/[CH:16]=[N:17]\[S:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[Si:1]([O:8][CH2:9][C@@H:10]([N:24]([CH2:37][CH:38]([CH3:40])[CH3:39])[S:25]([C:28]1[CH:36]=[CH:35][C:31]2[N:32]=[CH:33][S:34][C:30]=2[CH:29]=1)(=[O:27])=[O:26])[C:11]1[S:12][C:13]([CH2:16][NH:17][S:18]([C:20]([CH3:21])([CH3:22])[CH3:23])=[O:19])=[CH:14][CH:15]=1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 140656369HCID 140656369, compound

Product 1

HCID 131733467HCID 131733467, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-(5-{(Z)-[(tert-butylsulfinyl)imino]methyl}thiophen-2-yl)ethyl]-N-(2-methylpropyl)-1,3-benzothiazole-6-sulfonamide (1.78 g, 2.77 mmol) in MeOH (28 mL) at 0° C. was added NaBH4 (0.11 g, 2.77 mmol) and the reaction mixture was stirred for 4 hours before being quenched by the addition of water (50 mL). The slurry was stirred for 20 minutes, then extracted with ethyl acetate (3×100 mL). The organic layers were combined and dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude was purified on silica gel eluting with hexanes and ethyl acetate.

Workup

  1. custombefore being quenched by the addition of water (50 mL)
  2. stirringThe slurry was stirred for 20 minutes
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified on silica gel eluting with hexanes and ethyl acetate

Sources & evidence

ORD record
ord-9d41ab4b161943c19389de5a855e6bb9
Source dataset
uspto-grants-2015_09
Patent number
US09133157B2

Reaction notes

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