Toluene-4-sulfonic acid 2-(2-biphenyl-4-yl-methyl-oxazol-4-yl)ethyl ester → 3-(4-[2-(2-Biphenyl-4-yl-5-methyl-oxazol-4-yl)-ethoxy]-2-{[(2,5-dichloro-thiophene-3-carbonyl)-amino]-methyl}-phenyl)-propionic acid tert-butyl ester

HRID 1181056Notes

Reaction equation

HRID 1181056 reaction equation
[C:1]([O:5][C:6](=[O:27])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH2:16][NH:17][C:18]([C:20]1[CH:24]=[C:23]([Cl:25])[S:22][C:21]=1[Cl:26])=[O:19])([CH3:4])([CH3:3])[CH3:2].[C:28]1([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[CH:33]=[CH:32][C:31]([C:34]2[O:35][C:36]([CH3:52])=[C:37]([CH2:39][CH2:40]OS(C3C=CC(C)=CC=3)(=O)=O)[N:38]=2)=[CH:30][CH:29]=1>>[C:1]([O:5][C:6](=[O:27])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:40][CH2:39][C:37]2[N:38]=[C:34]([C:31]3[CH:32]=[CH:33][C:28]([C:53]4[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=4)=[CH:29][CH:30]=3)[O:35][C:36]=2[CH3:52])=[CH:11][C:10]=1[CH2:16][NH:17][C:18]([C:20]1[CH:24]=[C:23]([Cl:25])[S:22][C:21]=1[Cl:26])=[O:19])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 12966835Toluene-4-sulfonic acid 2-(2-biphenyl-4-yl-methyl-oxazol-4-yl)ethyl esterHCID 589791033-(2-{[(2,5-Dichloro-thiophene-3-carbonyl)-amino]-methyl}-4-hydroxy-phenyl)-propionic acid tert-butyl ester

Product 1

HCID 589792743-(4-[2-(2-Biphenyl-4-yl-5-methyl-oxazol-4-yl)-ethoxy]-2-{[(2,5-dichloro-thiophene-3-carbonyl)-amino]-methyl}-phenyl)-propionic acid tert-butyl esterYield 82%

Procedure

A mixture of 3-(2-{[(2,5-dichloro-thiophene-3-carbonyl)-amino]-methyl}-4-hydroxy-phenyl)-propionic acid tert-butyl ester (280 mg, 0.651 mmol) and toluene-4-sulfonic acid 2-(2-biphenyl-4-yl-5-methyl-oxazol-4-yl)-ethyl ester (498 mg, 1.15 mmol), were reacted according to Standard procedure A to give, after radial chromatography (hexanes/EtOAc 98:2 to 90:10), the title compound as a white solid (367 mg, 82%). 1H NMR (400 MHz, CDCl3): 1.36 (s, 9H), 2.37 (s, 3H), 2.55 (t, 2H, J=7.3 Hz), 2.87 (t, 2H, J=7.3 Hz), 2.96 (t, 2H, J=6.6 Hz), 4.22 (t, 2H, J=6.8 Hz), 4.58 (d, 2H, J=5.4 Hz), 6.80 (dd, 1H, J=8.3 Hz, J=2.4 Hz), 6.88 (d, 1H, J=2.9 Hz), 6.97 (t, 1H, J=5.9 Hz), 7.10 (d, 1H, J=8.8 Hz), 7.13 (s, 1H), 7.36 (t, 1H, J=7.3 Hz), 7.45 (t, 2H, J=7.8 Hz), 7.63 (d, 2H, J=8.3 Hz), 7.65 (d, 2H, J=6.3 Hz), 8.02 (d, 2H, J=7.8 Hz). MS (ES) m/e 691.2 [M+1].

Workup

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Sources & evidence

ORD record
ord-06496de126ba489d8951b83fae3b7ca5
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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