4-Chlorophenyl Isocyanate → methyl 2-(R)-{[4-(4-chlorophenylamino-carbonyl)piperazine-1-sulfonyl]amino}propionate

HRID 609711Notes

Reaction equation

HRID 609711 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[N:11]1([S:17]([NH:20][C@H:21]([CH3:26])[C:22]([O:24][CH3:25])=[O:23])(=[O:19])=[O:18])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>C(OCC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:14]2[CH2:15][CH2:16][N:11]([S:17]([NH:20][C@H:21]([CH3:26])[C:22]([O:24][CH3:25])=[O:23])(=[O:19])=[O:18])[CH2:12][CH2:13]2)=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 18727249methyl 2-(R)-[(piperazine-1-sulfonyl)amino]propionate

Product 1

HCID 18727239methyl 2-(R)-{[4-(4-chlorophenylamino-carbonyl)piperazine-1-sulfonyl]amino}propionateYield 55%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4-chlorophenylisocyanate (0.33 g, 2.14 mmol) in diethyl ether (30 ml) was added methyl 2-(R)-[(piperazine-1-sulfonyl)amino]propionate (0.42 g, 1.8 mmol) [prepared as described in Step 1 above]. The reaction was stirred at RT for 2 h and filtered. The solid was washed with additional ether and the solid was collected to give methyl 2-(R)-{[4-(4-chlorophenylamino-carbonyl)piperazine-1-sulfonyl]amino}propionate (55%). This material was converted to N-hydroxy-2-(R)-{[4-(4-chlorophenylaminocarbonyl)piperazine-1-sulfonyl]amino}propionamide by following Example 13.

Workup

  1. filtrationfiltered
  2. washThe solid was washed with additional ether
  3. customthe solid was collected

Sources & evidence

ORD record
ord-34308b0f55cf4bc892988e8d7b25375f
Source dataset
uspto-grants-1999_12
Patent number
US05998412

Reaction notes

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