Pyridine → HCID 57077207, compound

HRID 346364Notes

Reaction equation

HRID 346364 reaction equation
[N+:1]([C:4]1[CH:46]=[CH:45][C:7]([CH2:8][O:9][C:10]([NH:12][CH2:13][CH:14]([OH:44])[CH2:15][S:16][CH2:17][C@@H:18]2[CH2:22][C@@H:21]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:20][N:19]2[C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=2)=[O:32])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].N1C=CC=CC=1.[C:53](Cl)(=[O:55])[CH3:54]>ClCCl>[C:53]([O:44][CH:14]([CH2:13][NH:12][C:10]([O:9][CH2:8][C:7]1[CH:45]=[CH:46][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)=[O:11])[CH2:15][S:16][CH2:17][C@@H:18]1[CH2:22][C@@H:21]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:25])[CH3:26])[CH2:20][N:19]1[C:31]([O:33][CH2:34][C:35]1[CH:36]=[CH:37][C:38]([N+:41]([O-:43])=[O:42])=[CH:39][CH:40]=1)=[O:32])(=[O:55])[CH3:54]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 18641548HCID 18641548, compound

Product 1

HCID 57077207HCID 57077207, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4R)-2-[3-(4-nitrobenzyloxycarbonyl)amino-2-hydroxypropyl]thiomethyl-4-t-butyldimethylsilyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (2.24 g) in dichloromethane (40 ml) were added pyridine (0.52 ml) and acetyl chloride (0.46 ml) under ice-cooling with stirring. The mixture was stirred at the same temperature for 1 hour. The reaction mixture was washed with water, saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride, in turn, dried over anhydrous magnesium sulfate, and evaporated in vacuo to give (2S,4R)-2-[2-acetoxy-3-(4-nitrobenzyloxycarbonyl)aminopropyl]thiomethyl-4-t-butyldimethylsilyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (2.37 g).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at the same temperature for 1 hour
  3. washThe reaction mixture was washed with water, saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride, in turn
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-f50a5bb38a474ab989d1b7ea10aec147
Source dataset
uspto-grants-1991_10
Patent number
US05061804

Reaction notes

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