2-(4-((Tert-butoxycarbonyl)amino)phenyl)acetic acid → 3-{3-Benzyl-4-[2-(4-tert-butoxycarbonylamino-phenyl)-acetoxy]-phenyl}-2-ethoxy-propionic acid benzyl ester

HRID 1628161Notes

Reaction equation

HRID 1628161 reaction equation
[CH2:1]([O:8][C:9](=[O:29])[CH:10]([O:26][CH2:27][CH3:28])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30]([O:34][C:35]([NH:37][C:38]1[CH:43]=[CH:42][C:41]([CH2:44][C:45](O)=[O:46])=[CH:40][CH:39]=1)=[O:36])([CH3:33])([CH3:32])[CH3:31].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:29])[CH:10]([O:26][CH2:27][CH3:28])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:45](=[O:46])[CH2:44][C:41]2[CH:40]=[CH:39][C:38]([NH:37][C:35]([O:34][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:36])=[CH:43][CH:42]=2)=[C:14]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 28249932-(4-((Tert-butoxycarbonyl)amino)phenyl)acetic acidHCID 668644523-{3-Benzyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-acetoxy]-phenyl}-2-ethoxy-propionic acid benzyl esterHCID 668645693-(3-Benzyl-4-hydroxy-phenyl)-2-ethoxy-propionic acid benzyl ester

Product 1

HCID 668649273-{3-Benzyl-4-[2-(4-tert-butoxycarbonylamino-phenyl)-acetoxy]-phenyl}-2-ethoxy-propionic acid benzyl ester

Procedure

The title compound was prepared from 3-(3-benzyl-4-hydroxy-phenyl)-2-ethoxy-propionic acid benzyl ester (48 mg, 0.123 mol) and (4-tert-butoxycarbonylamino-phenyl)-acetic acid (31 mg, 0.123 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 (7:3) as the solvent to afford the product as a as an oil (65.1 mg, 72.2%). 1H NMR (400 MHz, CDCl3): δ 6.90-7.32 (m, 17H), 6.42 (br s, 1H), 5.08 (d, 2H), 3.97-3.98 (m, 1H), 3.73 s, 2H), 3.67 (s, 2H), 3.51-3.60 (m, 1H), 3.22-3.32 (m, 1H), 2.92-2.94 (m, 2H), 1.51 (s, 9H), 1.06-1.10 (t, 3H). Mass Spectrum: M−H+ 622.87.

Workup

  1. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-20238c101dc44d94afa18e08905f805a
Source dataset
uspto-grants-2014_07
Patent number
US08785681B2

Reaction notes

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