3-{3-Benzyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-acetoxy]-phenyl}-2-ethoxy-propionic acid benzyl ester → 4-[2-Ethoxy-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl]-benzoic acid 4-methane sulfonyloxy-benzyl ester
Reaction equation
[CH2:1]([O:3][CH:4]([C:15]([O:17][CH2:18][C:19]([Cl:22])([Cl:21])[Cl:20])=[O:16])[CH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)[CH3:2].O[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][S:32]([CH3:35])(=[O:34])=[O:33])=[CH:27][CH:26]=1.C(OC(=O)C(OCC)CC1C=CC(OC(=O)CC2N=C(C3C=CC=CC=3)OC=2C)=C(CC2C=CC=CC=2)C=1)C1C=CC=CC=1>>[CH3:35][S:32]([O:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][O:11][C:10](=[O:12])[C:9]2[CH:13]=[CH:14][C:6]([CH2:5][CH:4]([O:3][CH2:1][CH3:2])[C:15]([O:17][CH2:18][C:19]([Cl:20])([Cl:21])[Cl:22])=[O:16])=[CH:7][CH:8]=2)=[CH:26][CH:27]=1)(=[O:34])=[O:33]Participants
4
Reactant 3
Product 1
Procedure
The title compound was prepared from 4-[2-ethoxy-2-(2,2,2-trichloro-ethoxy carbonyl)-ethyl]-benzoic acid (0.032 g, 0.087 mmol) and methanesulfonic acid 4-hydroxymethyl-phenyl ester (0.018 g, 0.09 mmol) in the same manner as described for 3-{3-benzyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-acetoxy]-phenyl}-2-ethoxy-propionic acid benzyl ester. The crude product was purified by column chromatography using n-heptane/EtOAc (2:3) as the eluent to afford the title compound as a solid (0.023, 47%). 1H NMR (400 MHz, CDCl3): δ 7.96-7.98 (d, 2H), 7.47-7.49 (d, 2H), 7.33-7.35 (d, 2H), 7.27-7.29 (d, 2H), 5.33 (s, 2H), 4.68-4.81 (q, 2H), 4.15 (m, 1H), 3.65 (m, 1H), 3.32 (m, 1H), 3.08-3.15 (m, 2H), 3.13 (s, 3H), 1.13 (t, 3H).
Workup
- customThe crude product was purified by column chromatography
Sources & evidence
- ORD record
- ord-071fec2381fd4a4ba502b29baad55153
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181181B2
Reaction notes
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