5-(1-Benzyl-1H-indol-3-yl)-4-(7-phenyl-heptanoylamino)-pent-2-enoic acid methyl ester → (S)-5-(1-Benzyl-1H-indol-3-yl)-4-(7-phenyl-heptanoylamino)-pentanoic acid methyl ester

HRID 852852Notes

Reaction equation

HRID 852852 reaction equation
[CH3:1][O:2][C:3](=[O:39])[CH:4]=[CH:5][CH:6]([NH:24][C:25](=[O:38])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:9]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][C@H:6]([NH:24][C:25](=[O:38])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:9]=1

Participants

4

Reactant 1

HCID 694153865-(1-Benzyl-1H-indol-3-yl)-4-(7-phenyl-heptanoylamino)-pent-2-enoic acid methyl ester

Product 1

HCID 69414775(S)-5-(1-Benzyl-1H-indol-3-yl)-4-(7-phenyl-heptanoylamino)-pentanoic acid methyl esterYield 83.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-(1-Benzyl-1H-indol-3-yl)-4-(7-phenyl-heptanoylamino)-pent-2-enoic acid methyl ester (67 mg, 0.128 mmol) in MeOH (40 mL) was hydrogenated at 15 psi for 15 min using 10% Pd/C. The solution was filtered and the solvent removed to afford the title compound (56 mg, 83%), mp 107.1-109.2° C. 1H NMR (CDCl3) δ 1.21-1.34 (4H, m), 1.47-1.77 (5H, m), 1.87-1.98 (1H, m), 2.04 (2H, t, J=7.53 Hz), 2.26-2.44 (2H, m), 2.57 (2H, t, J=7.69 Hz), 2.91 (1H, dd, J=6.53, 14.63 Hz), 2.98 (1H, dd, J=5.52, 14.63 Hz), 3.62 (3H, s), 4.22-4.33 (1H, m), 5.26 (2H, s), 5.42 (1H, d, J=5.42), 6.96 (1H, s), 7.08-7.18 (7H, m), 7.24-7.28 (6H, m), 7.64 (1H, 7.26 Hz). 13C NMR (CDCl3) δ 174.3, 172.8, 142.7, 137.5, 136.6, 128.7, 128.6, 128.4, 128.2, 127.6, 126.8, 126.8, 125.6, 121.9, 119.3, 119.2, 110.8, 109.7, 51.7, 49.9, 49.5, 36.9, 35.8, 31.2, 31.0, 30.6, 29.1, 29.1, 28.9, 25.5. ISMS: 525 (M+H).

Workup

  1. filtrationThe solution was filtered
  2. customthe solvent removed

Sources & evidence

ORD record
ord-8ee560da3afc4d8eacd21ff77b2189a0
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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