2-(4-((Tert-butoxycarbonyl)amino)phenyl)acetic acid → 3-{4-[2-(4-tert-Butoxycarbonylamino-phenyl)-acetoxy]-3-methyl-phenyl}-2-ethoxy-propionic acid benzyl ester
Reaction equation
[CH2:1]([O:8][C:9](=[O:23])[CH:10]([O:20][CH2:21][CH3:22])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH3:19])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]([O:28][C:29]([NH:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][C:39](O)=[O:40])=[CH:34][CH:33]=1)=[O:30])([CH3:27])([CH3:26])[CH3:25].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>>[CH2:1]([O:8][C:9](=[O:23])[CH:10]([O:20][CH2:21][CH3:22])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:39](=[O:40])[CH2:38][C:35]2[CH:34]=[CH:33][C:32]([NH:31][C:29]([O:28][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:30])=[CH:37][CH:36]=2)=[C:14]([CH3:19])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Reactant 3
Product 1
Procedure
The title compound was prepared from 2-ethoxy-3-(4-hydroxy-3-methyl-phenyl)-propionic acid benzyl ester (38 mg, 0.15 mmol) and (4-tert-butoxycarbonylamino-phenyl)-acetic acid (47 mg, 0.15 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 product as a solid (32 mg, 85%). 1H NMR (400 MHz, CDCl3): δ 7.26-7.38 (m, 9H), 6.99-7.02 (m, 2H), 6.83-6.86 (d, 1H), 6.49 (br s, 1H), 5.12 (s, 2H), 4.00-4.05 (t, 1H), 3.80 (s, 2H), 3.58-3.61 (m, 1H), 3.31-3.36 (m, 1H), 2.94-2.96 (d, 2H), 1.98 (s, 3H), 1.52 (s, 9H), 1.12-1.16 (t, 3H).
Workup
- customThe crude product was purified by column chromatography
Sources & evidence
- ORD record
- ord-21c2ebc7b8d840969ec2ab0ebd65ebd9
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181181B2
Reaction notes
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