tert-Butyl 2-bromo-2-methylpropionate → (2S)-3-[4-(1-tert-butoxycarbonyl-1-methyl-ethoxy)-phenyl]-2-ethoxy-propionic acid ethyl ester

HRID 1353238Notes

Reaction equation

HRID 1353238 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C@@H:5]([O:14][CH2:15][CH3:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].[C:18]([O:22][C:23](=[O:28])[C:24](Br)([CH3:26])[CH3:25])([CH3:21])([CH3:20])[CH3:19].C(OC(=O)[C@@H](OC)CC1C=CC(OCC(OC(C)(C)C)=O)=CC=1)C>>[CH2:1]([O:3][C:4](=[O:17])[C@@H:5]([O:14][CH2:15][CH3:16])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][C:24]([C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:28])([CH3:26])[CH3:25])=[CH:11][CH:12]=1)[CH3:2]

Participants

4

Reactant 3

HCID 90290tert-Butyl 2-bromo-2-methylpropionateHCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 58864672(2S)-3-(4-tert-butoxycarbonylmethoxy-phenyl)-2-methoxy-propionic acid ethyl ester

Product 1

HCID 58646647(2S)-3-[4-(1-tert-butoxycarbonyl-1-methyl-ethoxy)-phenyl]-2-ethoxy-propionic acid ethyl ester

Procedure

The title compound was prepared (2S)-2-ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (example 251, step 3) and 2-bromo-2-methyl-propionic acid tert-butyl ester via the same procedure used to prepare (2S)-3-(4-tert-butoxycarbonylmethoxy-phenyl)-2-methoxy-propionic acid ethyl ester (PREPARATION 3, step 1) to produce a yellow oil.

Workup

  1. customto produce a yellow oil

Sources & evidence

ORD record
ord-1658b1535ec94faea768943bf05278d5
Source dataset
uspto-grants-2007_05
Patent number
US07220880B2

Reaction notes

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