L-Leucine → tert-Butyl N-[2-(4-{6-amino-5-[(4-fluorophenyl)carbonyl]-2-oxopyridin-1(2H)-yl}phenyl)ethyl]-L-leucinate

HRID 1667382Notes

Reaction equation

HRID 1667382 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.[NH2:31][C@H:32]([C:37]([OH:39])=[O:38])[CH2:33][CH:34]([CH3:36])[CH3:35]>>[NH2:1][C:2]1[N:7]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][NH:31][C@H:32]([C:37]([O:39][C:3]([CH3:22])([CH3:4])[CH3:2])=[O:38])[CH2:33][CH:34]([CH3:36])[CH3:35])=[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 6106L-LeucineHCID 58608538Methanesulfonic acid 2-{4-[6-amino-5-(4-fluoro-benzoyl)-2-oxo-2H-pyridin-1-yl]-phenyl}-ethyl ester

Product 1

HCID 57658410tert-Butyl 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 tbutyl ester. LC/MS: m/z 522 [M+H]+. 1H NMR (300 MHz, DMSO-d6) δ: 9.40-9.10 (2H, m), 7.59-7.44 (5H, m), 7.38-7.30 (4H, m), 5.71 (1H, d, J=9.6 Hz), 4.00 (1H, brs), 3.40-3.28 (1H, m), 3.25-3.15 (1H, m), 3.10-3.00 (2H, m), 1.80-1.70 (3H, m), 0.96 (6H, d, J=5.1 Hz).

Sources & evidence

ORD record
ord-74e8d25a164b477885b4090320d270d7
Source dataset
uspto-grants-2011_10
Patent number
US08044211B2

Reaction notes

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