1-Chloroethyl chloroformate → HCID 58042836, compound

HRID 564205Notes

Reaction equation

HRID 564205 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]([C:18]2[S:26][C:25]3[CH2:24][CH2:23][N:22](CC4C=CC=CC=4Cl)[CH2:21][C:20]=3[CH:19]=2)=[O:17])[C:11](=[O:35])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(OC(Cl)=O)C>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16](=[O:17])[C:18]2[S:26][C:25]3[CH2:24][CH2:23][NH:22][CH2:21][C:20]=3[CH:19]=2)[C:11](=[O:35])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformate3×HCID 67006867HCID 67006867, compound

Product 1

HCID 58042836HCID 58042836, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1.10 g (2.18 mmol) 4-benzyloxy-1-{2-[5-(2-chloro-benzyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridin-2-yl]-2-oxo-ethyl}-1H-pyridin-2-one (example 38.1a) in 20 mL DCM is added at 0° C. 0.29 mL (2.61 mL) chloro-formic acid 1-chloro-ethyl ester. The reaction mixture is stirred 60 h at RT. Additional 0.29 mL (2.61 mL) chloro-formic acid 1-chloro-ethyl ester is added and the mixture is stirred overnight. Additional 0.29 mL (2.61 mL) chloro-formic acid 1-chloro-ethyl ester is added and the reaction mixture is refluxed overnight. The solvent is removed, to the residue 30 mL of methanol are added and the reaction mixture is refluxed for 30 min. After cooling to RT, the precipitate is collected after cooling the mixture to RT, washed with cold methanol and dried.

Workup

  1. stirringthe mixture is stirred overnight
  2. temperaturethe reaction mixture is refluxed overnight
  3. customThe solvent is removed, to the residue 30 mL of methanol
  4. additionare added
  5. temperaturethe reaction mixture is refluxed for 30 min
  6. temperatureAfter cooling to RT
  7. customthe precipitate is collected
  8. temperatureafter cooling the mixture to RT
  9. washwashed with cold methanol
  10. customdried

Sources & evidence

ORD record
ord-e8ab109e573f4fbb9816bbe8aca2b78e
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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