Water → 1-[4-(Thiazol-5-yl)-phenyl]-4(S)-hydroxy-2-(tert-butoxycarbonyl)amino-5(S)-amino-6-phenyl-2-azahexane

HRID 1276967Notes

Reaction equation

[S:1]1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][N:13]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:14][C@H:15]([OH:31])[C@@H:16]([NH:24]C(=O)C(F)(F)F)[CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]1.C(Cl)Cl.O>CO>[S:1]1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][N:13]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:14][C@H:15]([OH:31])[C@@H:16]([NH2:24])[CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]1

Participants

Conditions

Temperature: 70 °C

Procedure

100 ml of a 1N KDCO3 solution are added dropwise to a solution of 5.646 g (10.0 mmol) of 1-[4-(thiazol-5-yl)-phenyl]-4(S)-hydroxy-2-(tert-butoxycarbonyl)amino-5(S)-(trifluoroacetyl)amino-6-phenyl-2-azahexane in 100 ml of methanol and the mixture is stirred at 70° C. for 15 hours. Methylene chloride and water are added; the aqueous phase is separated off and extracted 2× with methylene chloride. The organic phases are washed 2× with water, dried (Na2SO4) and concentrated by evaporation, yielding the title compound: Anal. (C25H32N4O3S (0.53 H2O)) calc. C 62.80, H 6.97, N 11.72, S 6.71, H2O 2.00: found C 63.2, H 7.01, N 11.57, S 6.49, H2O 1.98; HPLC20-100 : tRet =11.5.

Workup

customthe aqueous phase is separated off
extractionextracted 2× with methylene chloride
washThe organic phases are washed 2× with water
dry with materialdried (Na2SO4)
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-d72d7bc04def492883e51a007c19a7c7
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06166004

Reaction notes

Loading…