Thionyl Chloride → HCID 86602055, compound

HRID 1295371Notes

Reaction equation

HRID 1295371 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]2[C@@:10]([C:14](O)=[O:15])([CH2:11]2)[C@@H:9]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:25])=O>>[CH2:1]([N:8]1[CH2:13][CH:12]2[C@@:10]([C:14]([Cl:25])=[O:15])([CH2:11]2)[C@@H:9]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 69336894HCID 69336894, compound

Product 1

HCID 86602055HCID 86602055, compound

Procedure

To racemic Intermediate 39, one enantiomer being (1S,2S)-3-benzyl-2-phenyl-3-aza-bicyclo[3.1.0]hexane-1-carboxylic acid (0.16 g, 0.56 mmol) was added thionyl chloride (2 mL) dropwise with stirring. The homogeneous solution was refluxed gently for 2 hours. The solvent was removed at reduced pressure to yield the title compound (0.17 g, quantitative yield) as an oil, which was used without further purification.

Workup

  1. temperatureThe homogeneous solution was refluxed gently for 2 hours
  2. customThe solvent was removed at reduced pressure

Sources & evidence

ORD record
ord-4abcb740449947fcabb5fce84fb423fd
Source dataset
uspto-grants-2007_07
Patent number
US07241798B2

Reaction notes

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