HCID 13825248, compound → HCID 70045625, compound

HRID 1722313Notes

Reaction equation

[F:1][C:2]([F:18])([C@@H:7]([OH:17])[C@@H:8]([NH2:16])[CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[C:3]([NH:5][CH3:6])=[O:4].C(NC(=O)C(F)(F)[C@H](O)[C@@H](NC(OC(C)(C)C)=O)CC1CCCCC1)C>>[F:1][C:2]([F:18])([C@@H:7]([OH:17])[C@H:8]([NH2:16])[CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[C:3]([NH:5][CH3:6])=[O:4]

Participants

Reactant 2

HCID 13825248HCID 13825248, compound

HCID 18634309HCID 18634309, compound

Product 1

HCID 70045625HCID 70045625, compound

Procedure

An approximately 1:1 mixture (270 mg) of 2,2-difluoro-(R)-3-hydroxy-(S)-4-amino-5-cyclohexyl-N-methylvaleramide and 2,2-difluoro-(S)-3-hydroxy-(S)-4-amino-5-cyclohexyl-N-methylvaleramide obtained from 2,2-difluoro-(R,S)-3-hydroxy-4-t-butoxycarbonylamino-5-cyclohexyl-valeramide ethyl ester was treated according to the procedure of Example 1 with triethylamine, Mor-Phe-Nle, HBT and DCC to give, after identical workup and chromatography, the title substance (266 mg, 47%) which was well separated from the slightly less polar isomer (product of Example 1 (160 mg, 28%).

Sources & evidence

ORD record: ord-e34ca5a71c6d4e1782c37e2755157c15
Source dataset: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04855303

Reaction notes

Loading…