(S)-cyclopentyl 2-amino-4-methylpentanoate → Cyclopentyl(S)-2-(3-{4-[6-Amino-5-(4-fluoro-3-methylbenzoyl)-2-oxo-2H-pyridin-1-yl]-3,5-difluorophenoxy}propylamino)-4-methylpentanoate

HRID 1667369Notes

Reaction equation

HRID 1667369 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])=[C:29]([CH3:34])[CH:28]=1.[CH:36]1([O:41][C:42](=[O:49])[C@H:43]([CH2:45][CH:46]([CH3:48])[CH3:47])[NH2:44])[CH2:40][CH2:39][CH2:38][CH2:37]1>>[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:44][C@@H:43]([CH2:45][CH:46]([CH3:47])[CH3:48])[C:42]([O:41][CH:36]3[CH2:37][CH2:38][CH2:39][CH2:40]3)=[O:49])=[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])=[C:29]([CH3:34])[CH:28]=1

Participants

3

Reactant 2

HCID 53718217(S)-cyclopentyl 2-amino-4-methylpentanoate2×HCID 57658377Methanesulfonic acid 3-{4-[6-amino-5-(4-fluoro-3-methyl-benzoyl)-2-oxo-2H-pyridin-1-yl]-3,5-difluorophenoxy}propyl ester

Product 1

HCID 57658432Cyclopentyl(S)-2-(3-{4-[6-Amino-5-(4-fluoro-3-methylbenzoyl)-2-oxo-2H-pyridin-1-yl]-3,5-difluorophenoxy}propylamino)-4-methylpentanoate

Procedure

From Intermediate 4D and L-leucine cyclopentyl ester (Intermediate 8), LCMS purity 100%, m/z 614 [M+H]+, 1H NMR (400 MHz, d6-DMSO), δ: 0.90 (6H, m), 1.60-1.70 (10H, m), 1.90 (2H, m), 2.15 (2H, m), 2.30 (3H, s), 3.00-3.20 (2H, m), 4.10 (1H, s), 4.20 (2H, m), 5.25 (1H, m), 5.70 (1H, d), 7.05 (1H, d), 7.25 (1H, m), 7.40 (1H, m), 7.50 (1H, m), 7.60 (1H, d).

Sources & evidence

ORD record
ord-d6367e241a9a4b7cbba26c5b1ed273f2
Source dataset
uspto-grants-2011_10
Patent number
US08044211B2

Reaction notes

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