Methyl chloroformate → HCID 54355649, compound

HRID 2271024Notes

Reaction equation

HRID 2271024 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[NH2:6][CH2:7][CH2:8][S:9]([N:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@@H:14]([C:25]([NH:27][O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:26])[CH2:13]1)(=[O:11])=[O:10]>C(Cl)(Cl)Cl.N1C=CC=CC=1>[C:29]([O:28][NH:27][C:25]([C@H:14]1[CH2:13][N:12]([S:9]([CH2:8][CH2:7][NH:6][C:2]([O:4][CH3:5])=[O:3])(=[O:11])=[O:10])[CH2:17][CH2:16][N:15]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:26])([CH3:31])([CH3:32])[CH3:30]

Participants

5

Reactant 2

HCID 6586Methyl chloroformateHCID 54417248HCID 54417248, compound

Product 1

HCID 54355649HCID 54355649, compoundYield 102.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

Methyl chloroformate (132 mg) in CHCl3 (3 ml) was added dropwise to (2R)-4-(2-aminoethanesulfonyl)-N-tert-butoxy-1-tert-butoxycarbonyl-2-piperazinecarboxamide (400 mg) in pyridine (2.5 ml) with cooling on an ice bath. After stirring on the ice bath for 3 hours, the reaction mixture was concentrated in vacuo. The residue was partitioned between AcOEt and 3.6% HCl. The organic layer was washed with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution, dried over MgSO4, and concentrated in vacuo to give 470 mg of (2R)-N-tert-butoxy-1-tert-butoxycarbonyl-4-[2-(methoxycarbonylamino)ethanesulfonyl]-2-piperazinecarboxamide.

Workup

  1. temperaturewith cooling on an ice bath
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customThe residue was partitioned between AcOEt and 3.6% HCl
  4. washThe organic layer was washed with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-22e36b9062094035a7c964f923eb6f98
Source dataset
uspto-grants-2001_12
Patent number
US06333324B1

Reaction notes

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