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Benzyl chloroformate → (2S,3S)-1-[(benzyloxy)carbonyl]-3-hydroxypyrrolidine-2-carboxylic acid

HRID 737208
Notes
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Reaction equation

HRID 737208 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][NH:4][C@@H:3]1[C:7]([OH:9])=[O:8].CCN(C(C)C)C(C)C.Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]>CN(C=O)C>[CH2:23]([O:22][C:20]([N:4]1[CH2:5][CH2:6][C@H:2]([OH:1])[C@H:3]1[C:7]([OH:9])=[O:8])=[O:21])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 440575trans-3-hydroxy-L-proline

Product 1

HCID 54213972(2S,3S)-1-[(benzyloxy)carbonyl]-3-hydroxypyrrolidine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

(2S,3S)-3-Hydroxy-pyrrolidine-2-carboxylic acid (254.5 mg, 1.9 mmol) was dissolved in DMF (15 mL) and distilled water (6 mL). The solution was cooled to 0° C., and DIEA (500 μL, 2.9 mmol) was added followed by benzyl chloroformate (410 μL, 2.9 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 (6 mL)
  2. temperatureto warm to ambient temperature overnight
  3. filtrationThe reaction was filtered
  4. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-2b26034dabb1460bbd00f07fc96b6ccb
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07595398B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes