Methyl chloroformate → HCID 140448327, compound

HRID 1840603Notes

Reaction equation

HRID 1840603 reaction equation
Cl.[C:2]([C:5]1[CH:32]=[CH:31][C:8]([CH2:9][N:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[CH2:20][O:21][C:22]4[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:23]=4[CH:24]=3)(=[O:18])=[O:17])[CH2:12][C:11]2=[O:30])=[CH:7][CH:6]=1)(=[NH:4])[NH2:3].C(N(CC)CC)C.[C:40](Cl)(=[O:43])[O:41][CH3:42]>ClCCl>[Cl:29][C:27]1[CH:26]=[CH:25][C:23]2[CH:24]=[C:19]([S:16]([N:13]3[CH2:14][CH2:15][N:10]([CH2:9][C:8]4[CH:7]=[CH:6][C:5]([C:2](=[NH:3])[NH:4][C:40]([O:41][CH3:42])=[O:43])=[CH:32][CH:31]=4)[C:11](=[O:30])[CH2:12]3)(=[O:18])=[O:17])[CH2:20][O:21][C:22]=2[CH:28]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 23447334HCID 23447334, compound

Product 1

HCID 140448327HCID 140448327, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(4-amidinobenzyl)-4-(7-chloro-2H-benzopyran-3-sulfonyl)-2-piperazinone hydrochloride (99 mg) and triethylamine (0.084 ml) in dichloromethane (10 ml) was added dropwise a solution of methyl chlorocarbonate (0.023 g) in dichloromethane (2 ml) at 0 C., and the mixture was stirred at 0° C. for 1 hour. The reaction solution was diluted with dichloromethane, washed with sodium bicarbonate solution and saturated brine, dried (MgSO4) and concentrated. Precipitated crystals were washed with ether to give colorless crystals of the title compound (95 mg).

Workup

  1. washwashed with sodium bicarbonate solution and saturated brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customPrecipitated crystals
  5. washwere washed with ether

Sources & evidence

ORD record
ord-438dc931a5b14d4aa837bea63a10e258
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

Loading…