Benzyl chloroformate → HCID 66971092, compound

HRID 1361316Notes

Reaction equation

HRID 1361316 reaction equation
[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]([CH:20]2[CH2:25][CH2:24][C:23]([CH3:27])([CH3:26])[CH2:22][CH2:21]2)[C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:10][C@H:9]1[CH2:28][NH2:29])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl[C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32]>C(Cl)Cl>[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]([CH:20]2[CH2:25][CH2:24][C:23]([CH3:27])([CH3:26])[CH2:22][CH2:21]2)[C:14](=[O:19])[C:15]([CH3:17])([CH3:18])[CH3:16])[CH2:10][C@H:9]1[CH2:28][NH:29][C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 66970887HCID 66970887, compound

Product 1

HCID 66971092HCID 66971092, compoundYield 57,012.801%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4S)-1-BOC-2-(aminomethyl)-4-[(4,4-dimethylcyclohexyl)(2,2-dimethylpropanoyl)amino]pyrrolidine (410 mg, 1 mmol) prepared in Step A in DCM (10 ml) was slowly added dropwise benzyl chloroformate (200 mg, 1.2 mmol) at 0° C., and stirred at rt for 3 h. After the reaction finished, the solvent was concentrated in vacuo, the residue was extracted with water and EtOAc, and the organic layer was dried over MgSO4, concentrated in vacuo, and purified by column chromatography (eluent: EtOAc/Hex=1/1) to give the title compound (310 g, 72%).

Workup

  1. concentrationthe solvent was concentrated in vacuo
  2. extractionthe residue was extracted with water and EtOAc
  3. dry with materialthe organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography (eluent: EtOAc/Hex=1/1)

Sources & evidence

ORD record
ord-58302d81bded4c4a9803d6932207649a
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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