Trifluoroacetic acid → HDTrp-Leu-MetNH2 trifluoroacetate

HRID 2418575Notes

Reaction equation

[NH:1](C(OC(C)(C)C)=O)[C@@H:2]([C:13]([NH:15][C@H:16]([C:21]([NH:23][C@H:24]([C:29]([NH2:31])=[O:30])[CH2:25][CH2:26][S:27][CH3:28])=[O:22])[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42]>>[NH2:1][C@@H:2]([C:13]([NH:15][C@H:16]([C:21]([NH:23][C@H:24]([C:29]([NH2:31])=[O:30])[CH2:25][CH2:26][S:27][CH3:28])=[O:22])[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[F:39][C:40]([C:41]([OH:43])=[O:42])([F:45])[F:44]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 131713756BocDTrp-Leu-MetNH2

Product 1

HCID 131713755HDTrp-Leu-MetNH2 trifluoroacetateYield 50%

Procedure

Condensation of BocDTrpOPFP (2.35 g.) and HLeu-MetNH2 hydrochloride salt (Example 1, 1.49 g.) by the activated ester method gave BocDTrp-Leu-MetNH2 in 71% yield. De-t-butoxycarbonylation of BocDTrp-Leu-MetNH2 (1.75 g.) using trifluoroacetic acid gave HDTrp-Leu-MetNH2 trifluoroacetate salt in 50% yield.

Sources & evidence

ORD record: ord-b177be44b66e4b97b0d1a2da3b5e180c
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04472305

Reaction notes

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