Sodium borohydride → HCID 86669560, compound

HRID 524438Notes

Reaction equation

HRID 524438 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([O:31][CH:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[C:14]([NH:16][C:17]3[S:18][C:19]([O:22][C:23]4[CH:28]=[CH:27][C:26]([CH:29]=[O:30])=[CH:25][CH:24]=4)=[CH:20][N:21]=3)=[O:15])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[BH4-].[Na+]>CO.C(OCC)(=O)C>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([O:31][CH:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[C:14]([NH:16][C:17]3[S:18][C:19]([O:22][C:23]4[CH:28]=[CH:27][C:26]([CH2:29][OH:30])=[CH:25][CH:24]=4)=[CH:20][N:21]=3)=[O:15])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86669561HCID 86669561, compound

Product 1

HCID 86669560HCID 86669560, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(4-Cyclopropanesulfonyl-phenyl)-N-[5-(4-formyl-phenoxy)-thiazol-2-yl]-2-(tetrahydro-pyran-4-yloxy)-acetamide (Example A74; 0.2 g, 0.36 mmol) in 10 mL methanol, sodium borohydride (0.027 g, 0.73 mmol) was added in portions at 0° C. After complete addition reaction mixture was stirred for 1 hr at 0° C. to 10° C. Completion of the reaction was confirmed by TLC, then methanol was evaporated on rotavapour. Reaction mixture was diluted with ethyl acetate (3×20 mL), organic layer was washed with water and brine, dried (Na2SO4) and concentrated in vacuo. Purified by PREP TLC to afford title compound (0.110 g).

Workup

  1. customwas added in portions at 0° C
  2. additionAfter complete addition reaction mixture
  3. custommethanol was evaporated on rotavapour
  4. customReaction mixture
  5. washwas washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customPurified by PREP TLC

Sources & evidence

ORD record
ord-71859b693dd8428f8f239bf3e0d6edfc
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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