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

HRID 1458438Notes

Reaction equation

C([O-])([O-])=O.[K+].[K+].[S:7]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][N:19]([NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:20][C@H:21]([OH:37])[C@@H:22]([NH:30]C(=O)C(F)(F)F)[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:14][CH:13]=2)=[CH:10][N:9]=[CH:8]1.C(Cl)Cl.O>CO>[S:7]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][N:19]([NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:20][C@H:21]([OH:37])[C@@H:22]([NH2:30])[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:14][CH:13]=2)=[CH:10][N:9]=[CH:8]1

Participants

Conditions

Temperature: 70 °C

Procedure

100 ml of a 1N K2CO3 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-fb6b98d8f4664451a565feaff64f6001
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05849911

Reaction notes

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