Sodium Hydroxide → (4S)-5-[4-(Benzyloxy)phenyl]-4-(7-phenylheptanamido)pentanoic acid

HRID 852872Notes

Reaction equation

HRID 852872 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][CH2:5][C@H: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][C@@H: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 69414653HCID 69414653, compound

Product 1

HCID 446400(4S)-5-[4-(Benzyloxy)phenyl]-4-(7-phenylheptanamido)pentanoic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

(S)-5-(4-Benzyloxy-phenyl)-4-(7-phenyl-heptanoylamino)-pentanoic acid methyl ester (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 (63), 0.81 g (98%), m.p. 127.7-129.5° C. 1H NMR (DMSO-d6) δ 1.13-1.23 (6H, m, 3×CH2), 1.35-1.44 (2H, m, CH2), 1.47-1.54 (2H, m, CH2), 1.95-2.00 (2H, m, CH2), 2.14-2.22 (2H, m, CH2), 3.86 (1H, br s, H58□ 5.02 (2H, s, OCH2Ph), 6.89 (2H, d, J=8.6 Hz), 7.08 (2H, d, J=8.5 Hz), 7.15-7.44 (10H, m, 10×Ar—H), 7.50 (1H, br d, J=8.6 Hz, NH), 12.01 (1H, br s, CO2H). 13C NMR (DMSO-d6) δ 25.3, 28.4, 28.5, 29.3, 30.5, 31.0, 35.2, 35.5, 49.3, 114.3, 125.6, 127.7, 127.8, 128.2, 128.4, 130.1, 131.1, 137.2, 142.3, 156.7, 171.7, 174.3.

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, dried Na2SO4) and the solvent
  6. customremoved under reduced pressure

Sources & evidence

ORD record
ord-c86034a08361402a949966d2c31a66a6
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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