Phenyl thioxochloroformate → HCID 86598923, compound

HRID 456771Notes

Reaction equation

HRID 456771 reaction equation
[OH:1][C@H:2]1[C@H:7]2[CH2:8][C@H:4]([C@@H:5]([C:16]([O:18][CH3:19])=[O:17])[N:6]2[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.[C:20](Cl)(=[S:28])[O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>N1C=CC=CC=1>[O:21]([C:20]([O:1][C@H:2]1[C@H:7]2[CH2:8][C@H:4]([C@@H:5]([C:16]([O:18][CH3:19])=[O:17])[N:6]2[C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:3]1)=[S:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 70498Phenyl thioxochloroformateHCID 86598902HCID 86598902, compound

Product 1

HCID 86598923HCID 86598923, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-tert-butyl 3-methyl (1R,3S,4S, 6R)-6-hydroxy-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylate (4.5 g) in pyridine (10 mL), was added O-phenyl chlorothiocarbonate (3.15 g). The mixture was then stirred at room temperature for 3 hrs. The resulting mixture was evaporated in vacuo. To the residue, water was added. The mixture was extracted with ethyl acetate. The combined organic phase was washed successively with diluted hydrochloric acid, sodium hydrogen carbonate solution and brine, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with hexane and ethyl acetate (2:1) to give the target compound (5.22 g).

Workup

  1. customThe resulting mixture was evaporated in vacuo
  2. additionTo the residue, water was added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe combined organic phase was washed successively with diluted hydrochloric acid, sodium hydrogen carbonate solution and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with hexane and ethyl acetate (2:1)

Sources & evidence

ORD record
ord-6e63d73976cf4f6f942d2c86563bf83a
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

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