Methyl chloroformate → HCID 59610623, compound

HRID 417662Notes

Reaction equation

HRID 417662 reaction equation
[NH2:1][C@@H:2]([CH2:13][CH2:14][O:15][CH:16]([F:18])[F:17])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[CH3:19][O:20][C:21](Cl)=[O:22]>ClCCl>[F:18][CH:16]([F:17])[O:15][CH2:14][CH2:13][C@H:2]([NH:1][C:21]([O:20][CH3:19])=[O:22])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4]

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 67991507(S)-benzyl 2-amino-4-(difluoromethoxy)butanoate

Product 1

HCID 59610623HCID 59610623, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(S)-Benzyl 2-amino-4-(difluoromethoxy)butanoate (116 mg, 0.448 mmol) was dissolved in anhydrous dichloromethane (2.5 mL) and cooled down to 0° C. and TEA (181 mg, 1.79 mmol) and methylchloroformate (51 mg, 0.538 mmol) were added respectively. The mixture was stirred for 30 minutes and then it was stirred at room temperature overnight. The resulting product mixture was quenched with saturated NaHCO3 and extracted with dichloromethane. The organic layer was washed with saturated NH4Cl solution and brine and dried over Na2SO4. The volatiles were removed in vacuo to afford 56 mg (40%) of desired product after column purification.

Workup

  1. stirringit was stirred at room temperature overnight
  2. customThe resulting product mixture was quenched with saturated NaHCO3
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with saturated NH4Cl solution and brine
  5. dry with materialdried over Na2SO4
  6. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-62b426d4febe4ea68f6f2a9766510c94
Source dataset
uspto-grants-2012_01
Patent number
US08088368B2

Reaction notes

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