(R)-tert-Butyl 2-amino-4-methylpentanoate → tert-Butyl N-(3-{4-[6-amino-5-(2,4-difluorobenzoyl)-2-oxopyridin-1(2H)-yl]-3,5-difluorophenoxy}propyl)-D-leucinate

HRID 1667376Notes

Reaction equation

HRID 1667376 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:35])[C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=1[F:34].[C:36]([O:40][C:41](=[O:48])[C@@H:42]([CH2:44][CH:45]([CH3:47])[CH3:46])[NH2:43])([CH3:39])([CH3:38])[CH3:37]>>[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:43][C@@H:42]([C:41]([O:40][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:48])[CH2:44][CH:45]([CH3:46])[CH3:47])=[CH:10][C:9]=2[F:24])[C:6](=[O:25])[CH:5]=[CH:4][C:3]=1[C:26](=[O:35])[C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=1[F:34]

Participants

3

Reactant 2

HCID 7021798(R)-tert-Butyl 2-amino-4-methylpentanoateHCID 57658359HCID 57658359, compound

Product 1

HCID 57658354tert-Butyl N-(3-{4-[6-amino-5-(2,4-difluorobenzoyl)-2-oxopyridin-1(2H)-yl]-3,5-difluorophenoxy}propyl)-D-leucinate

Procedure

From Intermediate 4F and D-Leucine tert-butyl ester, LCMS purity 95%, m/z 606 [M+H]+, 1H NMR (300 MHz, DMSO), δ: 9.30-9.00 (2H, m), 7.62-7.52 (1H, m), 7.47-7.32 (2H, m), 7.28-7.12 (1H, m), 7.06 (2H, d, J=10.2 Hz), 5.73 (1H, d, J=9.6 Hz), 4.20 (2H, t, J=5.7 Hz), 3.99 (1H, br s), 3.25-2.95 (2H, m), 2.20-2.05 (2H, m), 1.80-1.60 (3H, m), 1.49 (9H, s), 0.95 (6H, d, J=4.8 Hz).

Sources & evidence

ORD record
ord-f948078935be429aa0dc2b875b7d7150
Source dataset
uspto-grants-2011_10
Patent number
US08044211B2

Reaction notes

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