Water → N2 (benzyloxycarbonyl)-N1-tert.butyl-4(S)-(methanesulphonyloxy)-L-prolinamide

HRID 466886Notes

Reaction equation

[N:1]#[N:2].[CH2:3]([O:10][C:11]([C@@:13]1([C:23]([NH2:25])=[O:24])[CH2:17][C@H:16]([OH:18])[CH2:15][N:14]1[C:19]([CH3:22])([CH3:21])[CH3:20])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:26][S:27](Cl)(=[O:29])=[O:28].O>N1C=CC=CC=1>[N:1]#[N:2].[CH2:3]([O:10][C:11]([C@@:13]1([C:23]([NH2:25])=[O:24])[CH2:17][C@H:16]([O:18][S:27]([CH3:26])(=[O:29])=[O:28])[CH2:15][N:14]1[C:19]([CH3:21])([CH3:22])[CH3:20])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

0.32 g of N2 -(benzyloxycarbonyl)-N1 -tert.butyl-4(S)-hydroxy-L-prolinamide was dissolved in 5 ml of dry pyridine while stirring, cooled to 0° C. and treated dropwise with 0.82 ml of methanesulphonyl chloride. The solution was stirred at 0° C. for a further 2 hours. The mixture was poured into a mixture of ice and water which was then extracted with ethyl acetate. The combined organic extracts were washed with 2M hydrochloric acid and then with saturated sodium bicarbonate solution and subsequently dried over anhydrous sodium sulphate. After evaporation there was obtained 0.5 g of N2 -(benzyloxycarbonyl)-N1 -tert.butyl-4(S)-(methanesulphonyloxy)-L-prolinamide as an oil which was used without further purification.

Workup

stirringThe solution was stirred at 0° C. for a further 2 hours
extractionwas then extracted with ethyl acetate
washThe combined organic extracts were washed with 2M hydrochloric acid
dry with materialwith saturated sodium bicarbonate solution and subsequently dried over anhydrous sodium sulphate
customAfter evaporation

Sources & evidence

ORD record: ord-b8ca2fa80a844197b0ffdaa036e90fd2
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05157041

Reaction notes

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