Ethyl chloroformate → HCID 178452182, compound

HRID 1361306Notes

Reaction equation

HRID 1361306 reaction equation
[C:1]([N:8]1[CH2:15][C@@H:14]([N:16]([C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[C@H:17]2[CH2:22][CH2:21][C@@H:20]([CH3:23])[CH2:19][CH2:18]2)[CH2:13][C@H:9]1[C:10](O)=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(OC(Cl)=O)C.O.[NH3:37]>C1COCC1>[C:1]([N:8]1[CH2:15][C@@H:14]([N:16]([C:24](=[O:29])[C:25]([CH3:26])([CH3:28])[CH3:27])[C@H:17]2[CH2:22][CH2:21][C@@H:20]([CH3:23])[CH2:19][CH2:18]2)[CH2:13][C@H:9]1[C:10]([NH2:37])=[O:11])([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 12896473Azane;hydrateHCID 178452183HCID 178452183, compound

Product 1

HCID 178452182HCID 178452182, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4S)-1-BOC-4-[(2,2-dimethylpropanoyl)(cis-4-methyl-cyclohexyl)amino]-L-proline (0.83 g, 2.05 mmol) prepared in Step C in THF was added dropwise TEA (0.32 ml, 2.27 mmol). Then, ethylchloroformate (0.24 g, 2.27 mmol) was slowly added dropwise at 0° C., and the reaction solution was stirred at the same temperature for 1 h. 28% Ammonia water (1 equivalent) was slowly added dropwise at 0° C., and stirred at the same temperature for additional 1 h. After the reaction finished, the reaction mixture was concentrated in vacuo, and extracted with EtOAC. The organic extracts were washed with brine, dried over MgSO4, concentrated in vacuo, and purified by column chromatography (eluent: EtOAc/Hex=2/1) to give the title compound (0.62 g, 74%).

Workup

  1. stirringstirred at the same temperature for additional 1 h
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. extractionextracted with EtOAC
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography (eluent: EtOAc/Hex=2/1)

Sources & evidence

ORD record
ord-bf5d8aec2bc749b39e58d33096539018
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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