Sodium borohydride → HCID 11443332, compound

HRID 2106431Notes

Reaction equation

HRID 2106431 reaction equation
[CH3:1][C:2]([CH3:36])([CH3:35])[C:3](=[O:34])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:17]2[O:18][C:19]3[CH:25]=[CH:24][C:23]([C:26]([NH:28][CH2:29][C:30]([OH:32])=[O:31])=[O:27])=[CH:22][C:20]=3[CH:21]=2)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:33].[BH4-].[Na+]>C1COCC1>[CH2:13]([C:12]([C:17]1[O:18][C:19]2[CH:25]=[CH:24][C:23]([C:26]([NH:28][CH2:29][C:30]([OH:32])=[O:31])=[O:27])=[CH:22][C:20]=2[CH:21]=1)([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH:3]([OH:34])[C:2]([CH3:35])([CH3:36])[CH3:1])=[C:7]([CH3:33])[CH:8]=1)[CH2:15][CH3:16])[CH3:14]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 11329383HCID 11329383, compound

Product 1

HCID 11443332HCID 11443332, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [(2-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethylpropyl}-benzofuran-5-carbonyl)-amino]-acetic acid (74 mg, 0.150 mmol) in THF (5.0 mL) at RT is treated with NaBH4 (11 mg, 0.300 mmol). The resulting mixture is stirred for 4 hour. The reaction is quenched with HCl (1.0 N, 1.0 mL) and extracted with EtOAc (2×20 mL). The organic layer is dried over Na2SO4, concentrated to afford the title compound (65 mg, 88%).

Workup

  1. customThe reaction is quenched with HCl (1.0 N, 1.0 mL)
  2. extractionextracted with EtOAc (2×20 mL)
  3. dry with materialThe organic layer is dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7fe6a0899ca8415aaea5fd9e098e096c
Source dataset
uspto-grants-2009_08
Patent number
US07579488B2

Reaction notes

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