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

HRID 1088954
Notes
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Reaction equation

HRID 1088954 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 10666767(2S,4R)-2-(carbamoylmethyl)thiomethyl-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 18641550(2S,4R)-2-(carbamoylmethyl)thiomethyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Reagents, catalysts & solvents

2
HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

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

  1. temperaturecooling
  2. waitto stand at ambient temperature for 1 hour
  3. washThe solution was washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes