4-Bromo-L-phenylalanine → (1S,5S) [1-{5-[(4-amino-benzenesulfonyl)-isobutyl-amino]-6-phosphonooxy-hexylcarbamoyl}-2-(4-bromo-phenyl)-ethyl]-carbamic acid methyl ester

HRID 1960093Notes

Reaction equation

HRID 1960093 reaction equation
[CH3:1][O:2][C:3](=[O:43])[NH:4][C@H:5]([C:14](=[O:42])[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][C@H:20]([N:27]([S:32]([C:35]1[CH:40]=[CH:39][C:38]([NH2:41])=[CH:37][CH:36]=1)(=[O:34])=[O:33])[CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:21][O:22][P:23]([OH:26])([OH:25])=[O:24])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1Br.C1C(C[C@H](N)C(O)=O)=CC=C([Br:56])C=1>>[CH3:1][O:2][C:3](=[O:43])[NH:4][C@H:5]([C:14](=[O:42])[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][C@H:20]([N:27]([S:32]([C:35]1[CH:40]=[CH:39][C:38]([NH2:41])=[CH:37][CH:36]=1)(=[O:33])=[O:34])[CH2:28][CH:29]([CH3:30])[CH3:31])[CH2:21][O:22][P:23]([OH:26])([OH:25])=[O:24])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Br:56])=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 6712144-Bromo-L-phenylalanineHCID 24999240(1s,5s)-[1-{5-[(4-Amino-benzenesulfonyl)-isobutyl-amino]-6-phosphonooxy-hexylcarbamoyl}-2-(2-bromo-phenyl)-ethyl]-carbamic acid methyl ester

Product 1

HCID 68474076(1S,5S) [1-{5-[(4-amino-benzenesulfonyl)-isobutyl-amino]-6-phosphonooxy-hexylcarbamoyl}-2-(4-bromo-phenyl)-ethyl]-carbamic acid methyl esterYield 28%

Procedure

This derivative was synthesized using the procedure described for the preparation of (1S,5S)-[1-{5-[(4-amino-benzenesulfonyl)-isobutyl-amino]-6-phosphonooxy-hexylcarbamoyl}-2-(2-bromo-phenyl)-ethyl]-carbamic acid methyl ester (example 4, steps A and B) using L-4-bromophenylalanine (Peptech Corp.) instead of L-2-bromophenylalanine. The desired material was obtained in 28% yield (25 mg)

Workup

  1. customThis derivative was synthesized

Sources & evidence

ORD record
ord-67c31c17cfbb42e1b758f838f0a5ac55
Source dataset
uspto-grants-2013_04
Patent number
US08410300B2

Reaction notes

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