Trifluoroacetic acid → HCID 131713738, compound

HRID 2418565Notes

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.FC(F)(F)C(O)=[O:42]>>[CH:10]1[CH:11]=[C:12]2[C:4]([CH2:3][CH:2]([NH2:1])[C:13]([OH:14])=[O:42])=[CH:5][NH:6][C:7]2=[CH:8][CH:9]=1.[NH2:15][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]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 131713739HCID 131713739, compound

Product 1

HCID 131713738HCID 131713738, compoundYield 81%

Procedure

Condensation of BocTrpOPFP (1.41 g.) and HLeu-Met-NH2 hydrochloride salt (Example 1, 0.89 g.) by the activated ester method gave BocTrp-Leu-MetNH2 in 81% yield. De-t-butoxycarbonylation of BocTrp-Leu-MetNH2 (1.06 g.) using trifluoroacetic acid containing 10% water gave Htrp-Leu-MetNH2 in 81% yield.

Sources & evidence

ORD record: ord-5a33ae192fc64e16b27ad155541e516f
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04472305

Reaction notes

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