3,5-Bis(benzyloxy)-alpha-chlorotoluene → [2-(3,4-Bis-benzyloxy-benzyloxy)-5-bromo-benzoylamino]-propionic acid methyl ester

HRID 2373842Notes

Reaction equation

HRID 2373842 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C@@H:4]([NH:18][C:19](=[O:28])[C:20]1[CH:25]=[C:24]([Br:26])[CH:23]=[CH:22][C:21]=1[OH:27])[CH2:5]C1C=CC(C2C=CC=CC=2)=CC=1.[CH2:30]([O:37][C:38]1[CH:43]=[CH:42][C:41]([CH2:44]Cl)=[CH:40][C:39]=1[O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[CH3:1][O:2][C:3](=[O:29])[CH:4]([NH:18][C:19](=[O:28])[C:20]1[CH:25]=[C:24]([Br:26])[CH:23]=[CH:22][C:21]=1[O:27][CH2:44][C:41]1[CH:42]=[CH:43][C:38]([O:37][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:39]([O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH:40]=1)[CH3:5]

Participants

3

Reactant 2

HCID 743393,5-Bis(benzyloxy)-alpha-chlorotolueneHCID 692047733-Biphenyl-4-yl-(2S)-(5-bromo-2-hydroxy-benzoylamino)-propionic acid methyl ester

Product 1

HCID 86597153[2-(3,4-Bis-benzyloxy-benzyloxy)-5-bromo-benzoylamino]-propionic acid methyl esterYield 61.1%

Procedure

3-Biphenyl-4-yl-2-S)-[2-(3,4-bis-benzyloxy-benzyloxy)-5-bromo-benzoylamino]-propionic acid methyl ester (340 mg) was prepared from 3-biphenyl-4-yl-2-(S)-(5-bromo-2-hydroxy-benzoylamino)-propionic acid methyl ester (400 mg, 0.92 mmol) (See example 136) and 1,2-bis-benzyloxy-4-chloromethyl-benzene (374 mg, 1.1 mmol) as described in general procedure G and purified over silica gel (8:2, DCM-hexanes).

Workup

  1. custompurified over silica gel (8:2, DCM-hexanes)

Sources & evidence

ORD record
ord-c17bc51b23d043a08ffa1a451d44ac03
Source dataset
uspto-grants-2008_12
Patent number
US07459472B2

Reaction notes

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