Thionyl Chloride → 61350-60-5

HRID 1611248Notes

Reaction equation

HRID 1611248 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-7b1509fd6ce941f1be3c1f12adce7045
Source dataset
uspto-grants-2006_01
Patent number
US06987104B2

Reaction notes

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