Benzyl Bromide → HCID 67086991, compound

HRID 1665145Notes

Reaction equation

HRID 1665145 reaction equation
[C:1]([N:8]1[C:12](=O)[CH2:11][CH2:10][C@@H:9]1[C:14]([O:16][CH2:17][CH3:18])=[O:15])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].BrCC1C=CC=CC=1.Br[C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:30][CH:29]=1>>[CH2:17]([O:16][C:14](=[O:15])[C@H:9]([NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:10][CH2:11][CH2:12][C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:30][CH:29]=1)[CH3:18]

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 8208851-Boc-D-Pyroglutamic acid ethyl esterHCID 27639591-Bromo-4-(tert-butoxy)benzene

Product 1

HCID 67086991HCID 67086991, compound

Procedure

(R)-2-tert-Butoxycarbonylamino-5-(4-tert-butoxy-phenyl)-pentanoic acid ethyl ester is prepared according to the procedure of Ding, Chuanyong.; Ma, Rujian.; Rong, Guobin. Preparation of w-Phenyl-(2S)—N-Boc-amino Acid Ethyl esters; Chinese Journal of Organic Chemistry Vol 26(12) 2006, 1694 &1695, replacing Ethyl Boc-L-pyroglutamate with Ethyl Boc-D-pyroglutamate & Bromomethyl-benzene with 1-Bromo-4-tert-butoxy-benzene in Example 2a, using preparation steps 2.2, 2.3, and 2.5; [M+H]+ 394

Workup

  1. customPreparation of w-Phenyl-(2S)—N-Boc-amino Acid Ethyl esters
  2. custompreparation steps 2.2, 2.3, and 2.5

Sources & evidence

ORD record
ord-56640144144444dfaf52bdfe79f35df8
Source dataset
uspto-grants-2011_10
Patent number
US08039472B2

Reaction notes

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