Trifluoroacetic acid → HCID 131713754, compound

HRID 2418574Notes

Reaction equation

[NH:1](C(OC(C)(C)C)=O)[C@@H:2]([C:13]([NH:15][C@H:16]([C:24]([O:26][CH3:27])=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[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:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38]>>[NH2:1][C@@H:2]([C:13]([NH:15][C@H:16]([C:24]([O:26][CH3:27])=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[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:35][C:36]([C:37]([OH:39])=[O:38])([F:41])[F:40]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 10576139HCID 10576139, compound

Product 1

HCID 131713754HCID 131713754, compoundYield 61%

Procedure

Condensation of BocDTrpOPFP (7.06 g.) and HPheOMe hydrochloride salt (3.24 g.) by the activated ester method gave BocDTrp-PheOMe in 81% yield. De-t-butoxycarbonylation of BocDTrp-PheOMe (5.0 g.) using trifluoroacetic acid gave HDTrp-PheOMe trifluoroacetate salt in 61% yield. Condensation of BocProOPFP (2.23 g.) and HDTrp-PheOMe trifluoroacetate salt (2.75 g.) by the activated ester method gave BocPro-DTrp-PheOMe in 74% yield. Hydrazinolysis of BocPro-DTrp-PheOMe (2.00 g.) gave BocPro-DTrp-PheNHNH2 yield.

Sources & evidence

ORD record: ord-ccc90081ddb148deb554523f1f77de58
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04472305

Reaction notes

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