Thionyl Chloride → 61350-60-5

HRID 1431938Notes

Reaction equation

HRID 1431938 reaction equation
[N:1]1([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3](O)=[O:4].S(Cl)([Cl:21])=O>C(Cl)Cl>[N:1]1([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([Cl:21])=[O:4]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 101987Benzyloxycarbonyl-L-proline

Product 1

HCID 1103285461350-60-5

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of Z-L-Pro-OH E-1 (10.0 g, 40.1 mmol, 1 equiv.) and thionyl chloride (30 mL, 401.2 mmol, 10 equiv.) in DCM (200 mL) is heated to reflux under nitrogen for 20 minutes and concentrated in vacuo. The residual oil is coevaporated with toluene 3×, and concentrated to give Z-L-Pro-Cl as an opaque oil.

Workup

  1. temperatureis heated
  2. temperatureto reflux under nitrogen for 20 minutes
  3. concentrationconcentrated in vacuo
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8b49e0889e424e8e8ecd2efe5b696ca1
Source dataset
uspto-grants-2009_11
Patent number
US07612059B2

Reaction notes

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