Chloroacetyl chloride → HCID 57870206, compound

HRID 1045703Notes

Reaction equation

HRID 1045703 reaction equation
Cl[CH2:2][C:3](Cl)=[O:4].[C:6]1([C@H:12]([NH:14][CH:15]2[CH2:19][O:18][CH2:17][CH:16]2[OH:20])[CH3:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.[OH-].[K+]>ClCCl.O>[C:6]1([C@H:12]([N:14]2[CH:15]3[CH:16]([CH2:17][O:18][CH2:19]3)[O:20][CH2:2][C:3]2=[O:4])[CH3:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 57870106HCID 57870106, compound

Product 1

HCID 57870206HCID 57870206, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Chloroacetyl chloride (0.88 ml, 11 mmol) was added to a solution of (3RS,4SR)-4-((1R)-1-phenyl-ethylamino)-tetrahydro-furan-3-ol (1.9 g, 9.2 mmol) and triethylamine (1.8 ml, 13 mmol) in dichloromethane (30 ml) at 0° C. and the solution was stirred for 2 hours at that temperature. The resulting mixture was poured into water and extracted with chloroform. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated. The crude material was dissolved into 2-propanol (30 ml) at room temperature and 85% potassium hydroxide (1.3 g, 20 mmol) was added to the resulting solution with vigorous stirring at room temperature. After 15 hours, the reaction mixture was poured into water and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting crude material was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=100/0 to 3/1) to yield (3aRS,7aSR)-7-((1R)-1-Phenyl-ethyl)-tetrahydro-2,4-dioxa-7-aza-inden-6-one (1.46 g, 5.9 mmol, 64%) as colorless oil.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. dissolutionThe crude material was dissolved into 2-propanol (30 ml) at room temperature
  5. stirringwith vigorous stirring at room temperature
  6. waitAfter 15 hours
  7. extractionextracted with ethyl acetate
  8. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting crude material was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=100/0 to 3/1)

Sources & evidence

ORD record
ord-1e9637fb1c2744f9854a6a6e09c9e224
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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