(S)-cyclopentyl 2-amino-4-methylpentanoate → Cyclopentyl N-[2-(4-{6-amino-5-[(4-fluorophenyl)carbonyl]-2-oxopyridin-1(2H)-yl}phenyl)ethyl]-L-leucinate

HRID 1667381Notes

Reaction equation

HRID 1667381 reaction equation
[NH2:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15]OS(C)(=O)=O)=[CH:10][CH:9]=2)[C:6](=[O:21])[CH:5]=[CH:4][C:3]=1[C:22](=[O:30])[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1.[CH:31]1([O:36][C:37](=[O:44])[C@H:38]([CH2:40][CH:41]([CH3:43])[CH3:42])[NH2:39])[CH2:35][CH2:34][CH2:33][CH2:32]1>>[NH2:1][C:2]1[N:7]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][NH:39][C@H:38]([C:37]([O:36][CH:31]3[CH2:32][CH2:33][CH2:34][CH2:35]3)=[O:44])[CH2:40][CH:41]([CH3:43])[CH3:42])=[CH:12][CH:13]=2)[C:6](=[O:21])[CH:5]=[CH:4][C:3]=1[C:22]([C:23]1[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=1)=[O:30]

Participants

3

Reactant 2

HCID 53718217(S)-cyclopentyl 2-amino-4-methylpentanoate2×HCID 58608538Methanesulfonic acid 2-{4-[6-amino-5-(4-fluoro-benzoyl)-2-oxo-2H-pyridin-1-yl]-phenyl}-ethyl ester

Product 1

HCID 57658470Cyclopentyl N-[2-(4-{6-amino-5-[(4-fluorophenyl)carbonyl]-2-oxopyridin-1(2H)-yl}phenyl)ethyl]-L-leucinate

Procedure

From Intermediate 4J and L-Leucine cyclopentyl ester (Intermediate 8). LC/MS: m/z 534 [M+H]+. 1H NMR (300 MHz, DMSO-d6) δ: 8.47 (1H, d, J=7.7 Hz), 7.56 (2H, m), 7.45 (1H, d, J=9.6 Hz), 7.38-7.24 (4H, m), 7.15 (2H, m), 5.69 (1H, d, J=9.8 Hz), 5.09 (1H, t, J=5.3 Hz), 4.63 (2H, m), 4.31 (1H, m), 1.84-1.79 (2H, m), 1.66-1.53 (9H, m), 0.92-0.86 (6H, m).

Sources & evidence

ORD record
ord-b92f1569b80744cf80561c210792a5fd
Source dataset
uspto-grants-2011_10
Patent number
US08044211B2

Reaction notes

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