Methanesulfonic acid 3-{4-[6-amino-5-(4-fluorobenzoyl)-2-oxo-2H-pyridin-1-yl]-3,5-difluorophenoxy}-propyl ester → Cyclopentyl(s)-(3-{4-[6-amino-5-(4-fluorobenzoyl)-2-oxo-2h-pyridin-1-yl]-3,5-difluorophenoxy}propylamino)phenylacetate

HRID 1667366Notes

Reaction equation

HRID 1667366 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.S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH:46]1([O:51][C:52](=[O:62])[C@H:53]([CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58]C=2)[NH2:54])[CH2:50][CH2:49][CH2:48][CH2:47]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:54][C@@H:53]([C:55]3[CH:56]=[CH:61][CH:60]=[CH:59][CH:58]=3)[C:52]([O:51][CH:46]3[CH2:47][CH2:48][CH2:49][CH2:50]3)=[O:62])=[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 57658362Methanesulfonic acid 3-{4-[6-amino-5-(4-fluorobenzoyl)-2-oxo-2H-pyridin-1-yl]-3,5-difluorophenoxy}-propyl esterHCID 86629432L-phenylalanine cyclopentyl ester tosylate2×

Product 1

HCID 57658303Cyclopentyl(s)-(3-{4-[6-amino-5-(4-fluorobenzoyl)-2-oxo-2h-pyridin-1-yl]-3,5-difluorophenoxy}propylamino)phenylacetate

Procedure

From Intermediate 4E and L-phenylalanine cyclopentyl ester tosylate salt (Intermediate 16), LCMS purity 97%, m/z 634 [M+H]+, 1H NMR (400 MHz, CD3OD), δ: 1.30-2.00 (8H, m), 2.30 (2H, m), 3.10 (1H, m), 3.40 (1H, m), 4.25 (2H, m), 4.40 (1H, m), 5.20 (1H, m), 5.85 (1H, d), 6.90 (2H, m), 7.10 (2H, d), 7.20-7.45 (7H, m), 7.65 (2H, m), 7.75 (1H, m).

Sources & evidence

ORD record
ord-54f13d79cd0e4c5a8dd74e0f21e53d86
Source dataset
uspto-grants-2011_10
Patent number
US08044211B2

Reaction notes

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