1-Chloroethyl chloroformate → HCID 66975154, compound

HRID 1022602Notes

Reaction equation

HRID 1022602 reaction equation
C([N:8]1[CH2:14][CH:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=2)[CH:12]([CH2:23][O:24][Si](C(C)(C)C)(C)C)[O:11][CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>C(#N)C>[ClH:21].[Cl:22][C:17]1[CH:16]=[C:15]([CH:13]2[CH:12]([CH2:23][OH:24])[O:11][CH2:10][CH2:9][NH:8][CH2:14]2)[CH:20]=[CH:19][C:18]=1[Cl:21]

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 66975148HCID 66975148, compound

Product 1

HCID 66975154HCID 66975154, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (6RS,7SR)-4-benzyl-7-({[tert-butyl(dimethyl)silyl]oxy}methyl)-6-(3,4-dichlorophenyl)-1,4-oxazepane (250 mg) in acetonitrile (1.5 mL) was added 1-chloroethyl chloroformate (0.0786 mL), and the mixture was stirred at room temperature for 1.5 hr. The solvent was evaporated under reduced pressure. To the residue was added methanol (1.5 ml), and the reaction mixture was stirred at 60° C. for 3 hr. The solvent was evaporated under reduced pressure. The residue was solidified with diisopropyl ether, and the obtained crude crystals were recrystallized from ethanol/ether/water to give the title compound (76.8 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionTo the residue was added methanol (1.5 ml)
  3. stirringthe reaction mixture was stirred at 60° C. for 3 hr
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained crude crystals
  6. customwere recrystallized from ethanol/ether/water

Sources & evidence

ORD record
ord-5df39f6e2bf54533b2102a212fabd748
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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