Triethylamine → (2S,4R)-2-(carbamoylmethyl)thiomethyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 1088954Notes

Reaction equation

[C:1]([CH2:4][S:5][CH2:6][C@@H:7]1[CH2:11][C@@H:10]([OH:12])[CH2:9][N:8]1[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)=[O:14])(=[O:3])[NH2:2].C(N(CC)CC)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35].C(OCC)(=O)C>O1CCCC1.CN(C)C=O>[C:1]([CH2:4][S:5][CH2:6][C@@H:7]1[CH2:11][C@@H:10]([O:12][S:34]([CH3:33])(=[O:36])=[O:35])[CH2:9][N:8]1[C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=1)=[O:14])(=[O:3])[NH2:2]

Participants

Conditions

Temperature: 2 °C

Procedure

To a solution of (2S,4R)-2-(carbamoylmethyl)thiomethyl-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.06 g) and triethylamine (0.92 ml) in a mixture of tetrahydrofuran (40 ml) and N,N-dimethylformamide (5 ml) was added dropwise methanesulfonyl chloride (0.44 ml) under ice-cooling. The mixture was stirred at 2° C. for 1 hour and then allowed to stand at ambient temperature for 1 hour. To the reaction mixture was added ethyl acetate (50 ml). The solution was washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride successively, dried over anhydrous magnesium sulfate, and evaporated in vacuo to give (2S,4R)-2-(carbamoylmethyl)thiomethyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.70 g).

Workup

temperaturecooling
waitto stand at ambient temperature for 1 hour
washThe solution was washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride successively
dry with materialdried over anhydrous magnesium sulfate
customevaporated in vacuo

Sources & evidence

ORD record: ord-0df653bcd9a94ccd98b8ab134d22ed8a
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04963543

Reaction notes

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