Sodium borohydride → HCID 68813830, compound

HRID 2106489Notes

Reaction equation

HRID 2106489 reaction equation
[CH3:1][C:2]([CH3:39])([CH3:38])[C:3](=[O:37])[CH2:4][CH2:5][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]([N:28]([CH2:30][C:31]([OH:33])=[O:32])[CH3:29])=[O:27])=[CH:22][C:20]=3[CH:21]=2)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH:34]([CH3:36])[CH3:35].[BH4-].[Na+]>C1COCC1>[CH2:13]([C:12]([C:17]1[O:18][C:19]2[CH:25]=[CH:24][C:23]([C:26]([N:28]([CH2:30][C:31]([OH:33])=[O:32])[CH3:29])=[O:27])=[CH:22][C:20]=2[CH:21]=1)([C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][CH:3]([OH:37])[C:2]([CH3:39])([CH3:1])[CH3:38])=[C:7]([CH:34]([CH3:35])[CH3:36])[CH:8]=1)[CH2:15][CH3:16])[CH3:14]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 68815476HCID 68815476, compound

Product 1

HCID 68813830HCID 68813830, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [(2-{1-[4-(4,4-Dimethyl-3-oxo-pentyl)-3-isopropyl-phenyl]-1-ethyl-propyl}-benzofuran-5-carbonyl)-methyl-amino]-acetic acid (27 mg, 0.05 mmol) (Example 55) in THF (2 mL) is treated with NaBH4 (4 mg, 0.1 mmol) at room temp. The resulting mixture is stirred for 2 hours. The mixture is concentrated and neutralized to pH 3 and extracted with EtOAc (3×5 mL). The organic layer is dried over sodium sulfate, concentrated to afford the desired compound. (17 mg, 63%) MS (ES) m/e: 536.3 (M−1)

Workup

  1. concentrationThe mixture is concentrated and neutralized to pH 3
  2. extractionextracted with EtOAc (3×5 mL)
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8f37f8c73f524e0eaebd801191131617
Source dataset
uspto-grants-2009_08
Patent number
US07579488B2

Reaction notes

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