Dimethylformamide → HCID 86750460, compound

HRID 975688Notes

Reaction equation

HRID 975688 reaction equation
C[C:2]([CH3:5])([O-])[CH3:3].[K+].[C:7]([OH:10])(=[S:9])[CH3:8].C(OC([N:17]1[CH2:21][C@H:20](OS(C)(=O)=O)[CH2:19][C@H:18]1[CH2:27][C:28]#[N:29])=O)C=C.[C:30](OCC)(=[O:32])C.CN(C)C=[O:39]>O>[C:7]([S:9][C@@H:20]1[CH2:21][N:17]([O:39][CH2:3][CH:2]=[CH2:5])[C@H:18]([CH2:27][C:28]#[N:29])[C:19]1=[C:30]=[O:32])(=[O:10])[CH3:8]

Participants

7

Reactant 5

HCID 6228Dimethylformamide2×HCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 54147914HCID 54147914, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 86750460HCID 86750460, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of potassium t-butoxide (2.18 g) and N,N-dimethylformamide (43 ml) was added thioacetic acid (1.48 g) at -10° C. After stirring at 0°-5° C. for 30 minutes, a solution of (2R,4R)-1-allyloxycarbonyl-2-cyanomethyl-4-methanesulfonyloxypyrrolidine (4.30 g) in N,N-dimethylformamide (4 ml) was added to the cold mixture. After stirring at 80° C. for 3 hours, the mixture was poured into a mixture of ethyl acetate and water. The separated organic layer was washed with aqueous sodium chloride solution twice, dried over magnesium sulfate and evaporated to give (2R,4S)-4-acetylthio-1-allyloxy-carbonyl-2-(cyanomethyl) pyrrolidine (4.04 g).

Workup

  1. stirringAfter stirring at 80° C. for 3 hours
  2. washThe separated organic layer was washed with aqueous sodium chloride solution twice
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-2017a3b5b15842adbe1c9b382d3921f2
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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