1-Chloroethyl chloroformate → HCID 136342089, compound

HRID 915977Notes

Reaction equation

HRID 915977 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[NH:25][C:26](=[O:40])[C:27]4[N:32]([CH:33]5[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]5)[N:31]=[C:30]([CH3:39])[C:28]=4[N:29]=3)=[C:20]([O:41][CH3:42])[CH:19]=2)(=[O:17])=[O:16])[CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:43]C(OC(Cl)C)=O>ClCCl>[ClH:43].[CH:33]1([N:32]2[C:27]3[C:26](=[O:40])[NH:25][C:24]([C:21]4[CH:22]=[CH:23][C:18]([S:15]([NH:14][CH:11]5[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]5)(=[O:17])=[O:16])=[CH:19][C:20]=4[O:41][CH3:42])=[N:29][C:28]=3[C:30]([CH3:39])=[N:31]2)[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 136005860HCID 136005860, compound

Product 1

HCID 136342089HCID 136342089, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 2 ml dichloromethane solution of 30 mg (0.05 mmol) of the compound obtained in Example 219, 11 μl (0.101 mmol) of 1-chloroethyl chloroformate was added, and the mixture was stirred at room temperature for 3 hours. Then, the reaction mixture was distilled under reduced pressure, 2 ml of methanol was added to the residue, and the mixture was heated under reflux for 3 hours. The reaction mixture was cooled to room temperature, and the solvent was distilled off under reduced pressure. The residue was recrystallized from ethanol to obtain 12 mg (45%) of the captioned compound.

Workup

  1. distillationThen, the reaction mixture was distilled under reduced pressure, 2 ml of methanol
  2. additionwas added to the residue
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 3 hours
  5. temperatureThe reaction mixture was cooled to room temperature
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-8bd7b49697174ccdb689f52875d92824
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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