Water → HCID 57293524, compound

HRID 346361Notes

Reaction equation

HRID 346361 reaction equation
[C:1]([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C@H:7]([CH2:23][O:24][CH2:25][CH2:26][OH:27])[CH2:6]1)(=[O:3])[CH3:2].ClS([N:32]=[C:33]=[O:34])(=O)=O.O>C(#N)C>[C:1]([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C@H:7]([CH2:23][O:24][CH2:25][CH2:26][O:27][C:33](=[O:34])[NH2:32])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 18641562HCID 18641562, compound

Product 1

HCID 57293524HCID 57293524, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (2S,4S)-4-acetylthio-2-(2-hydroxy-ethyloxymethyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.1 g) in acetonitrile (20 ml) was added chlorosulfonyl isocyanate(0.32 ml) at 0°-5° C. and the mixture was stirred at 20°-25° C. for 1 hour. Water (3 ml) was added to the solution at the same temperature and the mixture was stirred for 20 hours. After the solvent was evaporated, the residue was dissolved in ethyl acetate, washed with water, saturated sodium bicarbonate and brine successively. The dried organic layer was evaporated to give (2S,4S)-4-acetylthio-2-(2-carbamoyloxyethyloxymethyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.19 g).

Workup

  1. stirringthe mixture was stirred for 20 hours
  2. customAfter the solvent was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water, saturated sodium bicarbonate and brine successively
  5. customThe dried organic layer was evaporated

Sources & evidence

ORD record
ord-3e86076d1f864a098def4caf459a2762
Source dataset
uspto-grants-1991_10
Patent number
US05061804

Reaction notes

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