Ethanol → HCID 71183993, compound

HRID 1422604Notes

Reaction equation

HRID 1422604 reaction equation
[C:1]([CH2:3][CH:4]1[CH2:6][C:5]1([NH:16][C:17](=[O:20])[O:18][CH3:19])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1)#N.S(Cl)(Cl)=O.C([O-])(O)=[O:26].[Na+].[CH2:30]([OH:32])[CH3:31]>>[CH3:19][O:18][C:17]([NH:16][C:5]1([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=2)[CH2:6][CH:4]1[CH2:3][C:1]([O:32][CH2:30][CH3:31])=[O:26])=[O:20]

Participants

5

Reactant 4

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 78035676HCID 78035676, compound

Product 1

HCID 71183993HCID 71183993, compoundYield 98.1%

Conditions

Temperature
80 °C

Procedure

To a solution of methyl (1SR,2SR)-2-(cyanomethyl)-1-(3-nitrophenyl)cyclopropylcarbamate (intermediate B9a) (2.1 g, 7.63 mmol, Eq: 1.00) in ethanol (40 ml) was added dropwise thionyl chloride (13.6 g, 8.35 ml, 114 mmol, Eq: 15) ant the light brown solution was stirred at 80° C. for 1 hour. Poured cautiously into sat NaHCO3 solution, extracted with dichloromethane, washed the organic layer with brine and dried over Na2SO4. Removal of the solvent in vacuum left the ethyl 2-((1SR,2SR)-2-(methoxycarbonylamino)-2-(3-nitrophenyl)cyclopropyl)acetate (2.54 g, 7.49 mmol, 98.1% yield) as a light brown oil. MS (ISP): m/z=323.2 [(M+H)+].

Workup

  1. additionPoured cautiously
  2. extractionextracted with dichloromethane
  3. washwashed the organic layer with brine
  4. dry with materialdried over Na2SO4
  5. customRemoval of the solvent in vacuum

Sources & evidence

ORD record
ord-50019671b4924da883c7d989a45f7471
Source dataset
uspto-grants-2015_01
Patent number
US08927535B2

Reaction notes

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