Tetrahydrofuran → HCID 57810547, compound

HRID 2106490Notes

Reaction equation

HRID 2106490 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[CH:32]=[CH:31][C:20]3[CH:21]=[C:22]([C:24]([NH:26][CH2:27][C:28]([OH:30])=[O:29])=[O:25])[O:23][C:19]=3[CH:18]=2)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:33].[BH4-].[Na+].[CH2:39]1COCC1>>[CH2:15]([C:12]([C:17]1[CH:32]=[CH:31][C:20]2[CH:21]=[C:22]([C:24]([N:26]([CH2:27][C:28]([OH:30])=[O:29])[CH3:39])=[O:25])[O:23][C:19]=2[CH:18]=1)([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH:3]([OH:34])[C:2]([CH3:1])([CH3:35])[CH3:36])=[C:7]([CH3:33])[CH:8]=1)[CH2:13][CH3:14])[CH3:16]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 68815437HCID 68815437, compound

Product 1

HCID 57810547HCID 57810547, compoundYield 59%

Procedure

A solution of (6-{1-[4-(3,3-Dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-benzofuran-2-carbonyl)-amino]-acetic acid (66 mg, 0.130 mmol) (Example 57) in THF (2 mL) is treated with NaBH4 (11 mg, 0.26 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 (39 mg, 59%). MS (ES) m/e: 508.3 (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-f2a2d99223a34469946a5b40a2c9b685
Source dataset
uspto-grants-2009_08
Patent number
US07579488B2

Reaction notes

Loading…