Ethanol → 3-{3-Benzyl-4-[2-(4-tert-butoxycarbonylamino-phenyl)-acetoxy]-phenyl}-2-ethoxy-propionic acid

HRID 709502Notes

Reaction equation

HRID 709502 reaction equation
C([O:8][C:9](=[O:46])[CH:10]([O:43][CH2:44][CH3:45])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19](=[O:35])[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:23][CH:22]=2)=[C:14]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:13]=1)C1C=CC=CC=1.CCO>CCOC(C)=O>[CH2:36]([C:14]1[CH:13]=[C:12]([CH2:11][CH:10]([O:43][CH2:44][CH3:45])[C:9]([OH:46])=[O:8])[CH:17]=[CH:16][C:15]=1[O:18][C:19](=[O:35])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([O:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:29])=[CH:23][CH:22]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 668649273-{3-Benzyl-4-[2-(4-tert-butoxycarbonylamino-phenyl)-acetoxy]-phenyl}-2-ethoxy-propionic acid benzyl ester

Product 1

HCID 581194663-{3-Benzyl-4-[2-(4-tert-butoxycarbonylamino-phenyl)-acetoxy]-phenyl}-2-ethoxy-propionic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared from 3-{3-benzyl-4-[2-(4-tert-butoxycarbonylamino-phenyl)-acetoxy]-phenyl}-2-ethoxy-propionic acid benzyl ester (0.06 g, 0.096 mmol) in the same manner as described for example 1 with the difference that EtOH was used as the solvent instead of EtOAc. The crude product was purified by column chromatography using DCM/MeOH (9:1) as the eluent and the title compound was obtained as an oil (0.047 g, 24.2%). 1H NMR (400 MHz, CDCl3): δ 9.28 (s, 1H), 7.38-7.29 (d, 2H), 7.02-7.21 (m, 9H), 6.88-6.91 (d, 1H), 3.79 (s, 2H), 3.50-3.55 (m, 1H), 3.15-3.19 (m, 1H), 2.85-2.87 (dd, 1H), 2.64-2.69 (m, 1H), 2.48-2.50 (m, 1H), 1.45 (s, 9H), 0.91-0.95 (t, 3H). Mass spectrum: M−H+ 531.93.

Workup

  1. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-f4405841c0db406c9902c1992d8dedc9
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Reaction notes

Loading…