Benzyl chloroformate → (R)-3-((Benzyloxy)carbonyl)thiazolidine-4-carboxylic acid

HRID 737174

Reaction equation

HRID 737174 reaction equation
[S:1]1[CH2:5][C@@H:4]([C:6]([OH:8])=[O:7])[NH:3][CH2:2]1.CCN(C(C)C)C(C)C.Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>CN(C=O)C>[CH2:22]([O:21][C:19]([N:3]1[C@H:4]([C:6]([OH:8])=[O:7])[CH2:5][S:1][CH2:2]1)=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 93176L-Thioproline

Product 1

HCID 11119045(R)-3-((Benzyloxy)carbonyl)thiazolidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

(R)-Thiazolidine-4-carboxylic acid (309.9 mg, 2.33 mmol) was dissolved in DMF (10 mL) and distilled water (10 mL). The solution was cooled to 0° C., and DIEA (0.590 mL, 3.39 mmol) was added followed by benzyl chloroformate (0.485 mL, 3.40 mmol). The reaction was stirred at 0° C. and allowed to warm to ambient temperature overnight. The reaction was filtered and purified by reverse phase HPLC to give the desired product.

Workup

  1. distillationdistilled water (10 mL)
  2. temperatureto warm to ambient temperature overnight
  3. filtrationThe reaction was filtered
  4. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-aa810961bef348658de3df2fc279b3f4
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Linked notes

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