Methyl chloroformate → HCID 44126000, compound

HRID 1908638Notes

Reaction equation

HRID 1908638 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]([C:19](=[O:45])[C@@H:20]([NH:23][C:24]([C:26]2[CH:30]=[C:29]([O:31][CH2:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])[N:28]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[N:27]=2)=[O:25])[CH2:21][NH2:22])[CH2:15][CH2:14]1)=[O:12])[CH3:9].Cl[C:47]([O:49][CH3:50])=[O:48]>C(Cl)Cl.C(N(CC)CC)C>[CH2:8]([O:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]([C:19](=[O:45])[C@@H:20]([NH:23][C:24]([C:26]2[CH:30]=[C:29]([O:31][CH2:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])[N:28]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[N:27]=2)=[O:25])[CH2:21][NH:22][C:47]([O:49][CH3:50])=[O:48])[CH2:15][CH2:14]1)=[O:12])[CH3:9]

Participants

5

Reactant 2

HCID 6586Methyl chloroformateHCID 66920322HCID 66920322, compound

Product 1

HCID 44126000HCID 44126000, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 100 mg of 4-((S)-3-Amino-2-{[5-(3,3-dimethyl-2-oxo-butoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-propionyl)-piperazine-1-carboxylic acid ethyl ester trifluoroacetate in 2 ml DCM and 0.1 ml triethylamine, 20 mg methyl chloroformate was added at RT. After stirring for 4 h, the reaction mixture was concentrated under reduced pressure and purified by preparative HPLC (C18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA). The fractions containing the product were evaporated and lyophilized to yield a white solid. Yield: 19 mg

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. custompurified by preparative HPLC (
  3. washC18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA)
  4. additionThe fractions containing the product
  5. customwere evaporated
  6. customto yield a white solid

Sources & evidence

ORD record
ord-f07c315472d6432794ed8f1c87f5fffb
Source dataset
uspto-grants-2013_12
Patent number
US08598179B2

Reaction notes

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