Trifluoroacetic acid → H-D-Tyr-D-Ala-OMe

HRID 1395662Notes

Reaction equation

HRID 1395662 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@@H:2]([C:11]([OH:13])=O)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[NH2:21][C@@H:22]([C:24]([O:26][CH3:27])=[O:25])[CH3:23].FC(F)(F)C(O)=O>>[NH2:1][C@@H:2]([C:11]([NH:21][C@@H:22]([C:24]([O:26][CH3:27])=[O:25])[CH3:23])=[O:13])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 89020methyl D-alaninateHCID 1549481(2R)-2-(((tert-butoxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoic acid

Product 1

HCID 131711764H-D-Tyr-D-Ala-OMe

Procedure

t-Boc-D-Tyr-OH was coupled with D-Ala-OMe by the N-hydroxy-succinimide ester method (The Peptides, 1, p. 105). Deprotection was carried out using trifluoroacetic acid (The Peptides, 1, p. 39) and the resulting dipeptide methyl ester salt was purified by chromatography on Sephadex G-10 using 0.2 N HOAc.

Workup

  1. custom39) and the resulting dipeptide methyl ester salt was purified by chromatography on Sephadex

Sources & evidence

ORD record
ord-0efa0e861ab443f6b5fefde308e4517c
Source dataset
uspto-grants-1980_05
Patent number
US04205069

Reaction notes

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