Sodium Hydroxide → HCID 3477613, compound

HRID 852886Notes

Reaction equation

HRID 852886 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][CH2:5][CH:6]([NH:22][C:23](=[O:36])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=1.[OH-].[Na+]>CO.C1COCC1>[CH2:15]([O:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][CH:6]([NH:22][C:23](=[O:36])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:5][CH2:4][C:3]([OH:37])=[O:2])=[CH:9][CH:10]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69414655HCID 69414655, compound

Product 1

HCID 3477613HCID 3477613, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of (RS)-5-(4-Benzyloxy-phenyl)-4-(7-phenyl-heptanoylamino)-pentanoic acid methyl ester 78 (0.86 g, 1.7 mmol) and NaOH solution (4 M, 0.85 mL, 3.4 mmol) in MeOH-THF (1:1, 6 mL) was stirred at room temperature overnight. The solvent was removed, and the residue diluted with water. The solution was washed with Et2O, acidified with 5% aqueous HCl, and extracted with EtOAc. The organic phase was then washed with brine, dried (Na2SO4) and the solvent removed under reduced pressure to afford 85 (0.81 g, 98%), m.p. 127.7-129.5° C. 1H NMR (DMSO-d6) δ 1.13-1.23 (m, 6H), 1.35-1.44 (m, 2H), 1.47-1.54 (m, 2H), 1.95-2.00 (m, 2H), 2.14-2.22 (m, 2H), 3.86 (br s, 1H), 5.02 (s, 2H), 6.89 (d, J=8.6 Hz, 2H), 7.08 (d, J=8.5 Hz, 2H), 7.15-7.44 (m, 10H), 7.50 (br d, J=8.6 Hz, 1H), 12.01 (br s, 1H). 13C NM (DMSO-d6) δ 174.3, 171.7, 156.7, 142.3, 137.2, 131.1, 130.1, 128.4, 128.2, 127.8, 127.7, 125.6, 114.3, 49.3, 35.5, 35.2, 31.0, 30.5, 29.3, 28.5, 28.4, 25.3. ESMS 488 (M+H)+.

Workup

  1. customThe solvent was removed
  2. additionthe residue diluted with water
  3. washThe solution was washed with Et2O
  4. extractionextracted with EtOAc
  5. washThe organic phase was then washed with brine
  6. dry with materialdried (Na2SO4)
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-9981c9f8ea17467a9430ad504bfa0446
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

Loading…