Allyl chloroformate → HCID 86760498, compound

HRID 1766905Notes

Reaction equation

HRID 1766905 reaction equation
C(OC([NH:8][C@H:9]([C:18](=[O:25])[O:19][CH2:20][C:21]([Cl:24])([Cl:23])[Cl:22])[CH2:10][C:11]([O:13][C:14]([CH3:17])(C)C)=[O:12])=O)(C)(C)C.[CH:26](N(C(C)C)CC)(C)C.Cl[C:36]([O:38][CH2:39][CH:40]=[CH2:41])=[O:37].[Cl-].[NH4+]>FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>[CH2:39]([O:38][C:36]([NH:8][C@H:9]([C:18](=[O:25])[O:19][CH2:20][C:21]([Cl:22])([Cl:23])[Cl:24])[CH2:10][C:11]([O:13][CH2:14][CH:17]=[CH2:26])=[O:12])=[O:37])[CH:40]=[CH2:41]

Participants

7

Reactant 4

HCID 18052Allyl chloroformateHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 58885434HCID 58885434, compound

Product 1

HCID 86760498HCID 86760498, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl (S)-3-[(tert-butyl)oxycarbonylamino]-4-oxo-4-(2,2,2-trichloroethoxy)butyrate (605 mg, 1.48 mmol) obtained from Example 20-(1) was dissolved in trifluoroacetic acid (2.5 ml) followed by stirring for 1 hour. The mixture was diluted with toluene, and the solvent was distilled off under reduced pressure. The obtained white powder was suspended in dichloromethane (5 ml), and diisopropylethylamine (1.8 ml, 10 mmol) and allyl chloroformate (624 mg, 5.18 mmol) were added thereto at room temperature. The mixture was stirred for 1 hour, then a saturated aqueous solution of ammonium chloride was added thereto, and the product was extracted with ethyl acetate. The organic layer was washed successively with water and an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was subjected to chromatography on a silica gel (25 g) column (eluent; hexane:ethyl acetate=4:1) to afford the title compound (384 mg, 67% yield) as a colorless oil.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. customat room temperature
  3. stirringThe mixture was stirred for 1 hour
  4. extractionthe product was extracted with ethyl acetate
  5. washThe organic layer was washed successively with water
  6. dry with materialan aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-097b963a52024d788ac0fce29155fe75
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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