Water → HCID 57046045, compound

HRID 37274Notes

Reaction equation

HRID 37274 reaction equation
[OH:1][CH2:2][C:3]1[S:4][CH:5]=[C:6]([C@@H:8]2[CH2:12][C@@H:11]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10][N:9]2[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)=[O:19])[N:7]=1.ClS([N:35]=[C:36]=[O:37])(=O)=O.O>C(#N)C>[C:36]([O:1][CH2:2][C:3]1[S:4][CH:5]=[C:6]([C@@H:8]2[CH2:12][C@@H:11]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10][N:9]2[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)=[O:19])[N:7]=1)(=[O:37])[NH2:35]

Participants

5

Reactant 3

HCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 15077763(2S,4R)-2-[2-(hydroxymethyl)thiazol-4-yl]-4-(methanesulfonyloxy)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 57046045HCID 57046045, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (2S, 4R)-2-[2-(hydroxymethyl)-thiazol-4-yl]-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl) pyrrolidine (2.1 g) in acetonitrile (50 ml) was added chlorosulfonyl isocyanate (0.48 ml) at 0°-5° C. and the mixture was stirred at ambient temperature 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 removed, the residue was dissolved in ethyl acetate, and washed with water, saturated sodium bicarbonate and brine successively. The dried organic layer was evaporated to give (2S,4R)2- [2-(carbamoyloxymethyl)thiazol-4-yl]-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl) pyrrolidine (2.2 g).

Workup

  1. stirringthe mixture was stirred for 20 hours
  2. customAfter the solvent was removed
  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-bbf1bfa716414f1586bdc97e0a6bc4f7
Source dataset
uspto-grants-1995_05
Patent number
US05420122

Reaction notes

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