Sodium borohydride → HCID 11466261, compound

HRID 2106435Notes

Reaction equation

HRID 2106435 reaction equation
[N:1]1[NH:2][N:3]=[N:4][C:5]=1[NH:6][C:7]([C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([C:17]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])=[C:24]([CH3:36])[CH:23]=3)([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:14][C:13]=2[CH:37]=1)=[O:8].[BH4-].[Na+]>C1COCC1>[N:4]1[NH:3][N:2]=[N:1][C:5]=1[NH:6][C:7]([C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([C:17]([CH2:18][CH3:19])([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH:30]([OH:35])[C:31]([CH3:33])([CH3:34])[CH3:32])=[C:24]([CH3:36])[CH:23]=3)[CH2:20][CH3:21])=[CH:14][C:13]=2[CH:37]=1)=[O:8]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 11225866HCID 11225866, compound

Product 1

HCID 11466261HCID 11466261, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-benzofuran-5-carboxylic acid (2H-tetrazol-5-yl)-amide (90 mg, 0.179 mmol) in THF (5.0 mL) at RT is treated with NaBH4 (20 mg, 0.537 mmol). The resulting mixture is stirred for 30 min. The reaction is quenched with water (1.0 mL) and extracted with EtOAc (2×20 mL). The organic layer is dried over Na2SO4, concentrated to afford the title compound (35 mg, 39%).

Workup

  1. customThe reaction is quenched with water (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-b73abcdcf3f944c197c2cedfa2a1c8f9
Source dataset
uspto-grants-2009_08
Patent number
US07579488B2

Reaction notes

Loading…