Methyl chloroformate → HCID 22790257, compound

HRID 1076647Notes

Reaction equation

HRID 1076647 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+].[C:12]1([CH:18]2[NH:22][C@H:21]([C:23]([OH:25])=[O:24])[CH2:20][S:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl[C:27]([O:29][CH3:30])=[O:28]>CCOCC.O>[C:12]1([CH:18]2[N:22]([C:27]([O:29][CH3:30])=[O:28])[C@H:21]([C:23]([OH:25])=[O:24])[CH2:20][S:19]2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 6586Methyl chloroformateHCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 11009168(4R)-2-phenyl-1,3-thiazolidine-4-carboxylic acid

Product 1

HCID 22790257HCID 22790257, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 60 g. of sodium carbonate in 330 ml. of water and 220 ml. of 10% sodium bicarbonate was added 62.7 g. (.3 mole) of 2-phenyl-4-(R)-carboxythiazolidine. A solution of 23.0 ml. (28.4 g., 0.3 mole) of methyl chloroformate in 75 ml. of ether was added dropwise over 30 minutes. The reaction mixture was stirred at room temperature for one additional hour. The entire reaction mixture, including some solid which occasionally separated, was acidified carefully (foaming) to pH 1 by the dropwise addition of about 50 ml. of 6N HCl. The reaction was extracted 3 × 300 ml. portions of methylene chloride. The organic phases were dried over sodium sulfate and evaporated to afford 77.4 g (97%) of the 2-phenyl-3-carbomethoxy-4-(R)-carboxythiazolidine as a white crystalline solid, having a m.p. of 129°-130°C.

Workup

  1. additionTo a mixture of 60 g
  2. customThe entire reaction mixture
  3. customoccasionally separated
  4. additionby the dropwise addition of about 50 ml
  5. extractionThe reaction was extracted 3 × 300 ml
  6. dry with materialThe organic phases were dried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-678bcdc14211427dbe4d72253fd62c9d
Source dataset
uspto-grants-1976_05
Patent number
US03957794

Reaction notes

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