Succinic anhydride → (S)-4-(4-(2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-methoxy-3-oxopropyl)phenylamino)-4-oxobutanoic acid

HRID 2197391Notes

Reaction equation

HRID 2197391 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[CH:8]1[C:20]2[CH:19]([CH2:21][O:22][C:23]([NH:25][C@@H:26]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=3)[C:27]([O:29][CH3:30])=[O:28])=[O:24])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]=2[CH:11]=[CH:10][CH:9]=1>>[CH:8]1[C:20]2[CH:19]([CH2:21][O:22][C:23]([NH:25][C@H:26]([C:27]([O:29][CH3:30])=[O:28])[CH2:31][C:32]3[CH:33]=[CH:34][C:35]([NH:38][C:4](=[O:5])[CH2:3][CH2:2][C:1]([OH:6])=[O:7])=[CH:36][CH:37]=3)=[O:24])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]=2[CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 7922Succinic anhydrideHCID 14284323(S)-methyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-aminophenyl)propanoate

Product 1

HCID 59367368(S)-4-(4-(2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-methoxy-3-oxopropyl)phenylamino)-4-oxobutanoic acidYield 66%

Procedure

Succinic anhydride (6.72 g, 67.2 mmol) was added to the solution of (S)-methyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-aminophenyl)propanoate 3C from step 2. The reaction mixture was stirred at room temperature overnight. The solvent was removed, and the residual solid was washed with 30% ethyl acetate/petroleum ether (200 mL) and recrystallized in THF and 30% ethyl acetate/petroleum ether to give (S)-4-(4-(2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-methoxy-3-oxopropyl)phenylamino)-4-oxobutanoic acid 3D as a white solid (19 g, 66% yield). 1HNMR (DMSO-d6, 300 MHz) δ: 10-9.9 (s, 1H), 8.0-7.9 (m, 3H), 7.8-7.6 (m, 2H), 7.6-7.5(m, 2H), 7.5-7.4(m, 2H), 7.4-7.3(m, 2H), 7.3-7.1(d, 2H), 4.4-4.2 (m, 4H), 3.8-3.6 (s, 3H), 3.1-2.8 (m, 2H), 2.7-2.5 (m, 4H); ESI-MS: m/z 517.3 (M+H)+.

Workup

  1. customThe solvent was removed
  2. washthe residual solid was washed with 30% ethyl acetate/petroleum ether (200 mL)
  3. customrecrystallized in THF

Sources & evidence

ORD record
ord-e4d4c57636b24f16bbf1f92091c2f244
Source dataset
uspto-grants-2012_12
Patent number
US08338565B2

Reaction notes

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