L-Leucine ethyl ester → Ethyl N-(3-{4-[6-amino-5-(4-fluorobenzoyl)-2-oxopyridin-1(2H)-yl]-3,5-difluorophenoxy}propyl)-L-leucinate

HRID 1667367Notes

Reaction equation

HRID 1667367 reaction equation
[NH2:1][C:2]1[N:7]([C:8]2[C:22]([F:23])=[CH:21][C:11]([O:12][CH2:13][CH2:14][CH2:15]OS(C)(=O)=O)=[CH:10][C:9]=2[F:24])[C:6](=[O:25])[CH:5]=[CH:4][C:3]=1[C:26](=[O:34])[C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1.[CH2:35]([O:37][C:38](=[O:45])[C@H:39]([CH2:41][CH:42]([CH3:44])[CH3:43])[NH2:40])[CH3:36]>>[NH2:1][C:2]1[N:7]([C:8]2[C:22]([F:23])=[CH:21][C:11]([O:12][CH2:13][CH2:14][CH2:15][NH:40][C@H:39]([C:38]([O:37][CH2:35][CH3:36])=[O:45])[CH2:41][CH:42]([CH3:44])[CH3:43])=[CH:10][C:9]=2[F:24])[C:6](=[O:25])[CH:5]=[CH:4][C:3]=1[C:26](=[O:34])[C:27]1[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=1

Participants

3

Reactant 2

HCID 75971L-Leucine ethyl esterHCID 57658362Methanesulfonic acid 3-{4-[6-amino-5-(4-fluorobenzoyl)-2-oxo-2H-pyridin-1-yl]-3,5-difluorophenoxy}-propyl ester

Product 1

HCID 57658386Ethyl N-(3-{4-[6-amino-5-(4-fluorobenzoyl)-2-oxopyridin-1(2H)-yl]-3,5-difluorophenoxy}propyl)-L-leucinate

Procedure

From Intermediate 4E and L-leucine ethyl ester LCMS purity 98%, m/z 560 [M+H]+, 1H NMR (400 MHz, CD3OD), δ: 1.10-1.20 (6H, m), 1.45-1.55 (3H, t), 1.65-1.85 (2H, m), 1.90-2.00 (1H, m), 2.15-2.30 (2H, m), 2.85-3.05 (2H, m), 3.55 (1H, m), 4.35-4.50 (4H, m), 6.00 (1H, d), 7.10 (1H, d), 7.45-7.55 (1H, m), 7.80-7.85 (1H, m), 7.95 (1H, d).

Sources & evidence

ORD record
ord-c280d596d1b4475db4384aca556835d9
Source dataset
uspto-grants-2011_10
Patent number
US08044211B2

Reaction notes

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