Methyl chloroformate → HCID 178500864, compound

HRID 278617Notes

Reaction equation

HRID 278617 reaction equation
[C:1]([NH:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([N:13]2[CH2:18][CH2:17][N:16]([S:19]([C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[CH:25][CH:26]=[C:27]([Cl:32])[CH:28]=4)[CH:23]=3)(=[O:21])=[O:20])[CH2:15][CH2:14]2)=[O:12])[CH2:7][CH2:6]1)(=[NH:3])[CH3:2].C(N(CC)CC)C.[C:40](Cl)(=[O:43])[O:41][CH3:42]>ClCCl>[CH3:42][O:41][C:40]([CH2:2][C:1]([NH:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([N:13]2[CH2:18][CH2:17][N:16]([S:19]([C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[CH:25][CH:26]=[C:27]([Cl:32])[CH:28]=4)[CH:23]=3)(=[O:21])=[O:20])[CH2:15][CH2:14]2)=[O:12])[CH2:7][CH2:6]1)=[NH:3])=[O:43]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 178465617HCID 178465617, compound

Product 1

HCID 178500864HCID 178500864, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(trans-4-acetimidoylaminocyclohexane-1-ylcarbonyl)-4-(6-chloronaphthalene-2-sulfonyl)piperazine (300 mg) and triethylamine (199 mg) in dichloromethane (30 ml) was added methyl chlorocarbonate (192 mg), and the mixture was stirred at room temperature for 30 minutes. The reaction solution was concentrated, and the residue was purified with silica gel column chromatography (ethyl acetate) to give colorless crystals of the title compound (171 mg).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe residue was purified with silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-b1e38f08961c4983a8997215b5e121d8
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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