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Chloroform → N-acetyl-4-hydroxy-L-proline ethyl ester

HRID 1723899
Notes
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Reaction equation

HRID 1723899 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].Cl.[CH2:9]([O:11][C:12](=[O:19])[C@@H:13]1[CH2:17][CH:16]([OH:18])[CH2:15][NH:14]1)[CH3:10].C(N(CC)CC)C.C(Cl)(Cl)Cl>O>[CH2:9]([O:11][C:12](=[O:19])[C@@H:13]1[CH2:17][CH:16]([OH:18])[CH2:15][N:14]1[C:1](=[O:3])[CH3:2])[CH3:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6212ChloroformHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 127093054hydroxy-L-proline ethyl ester hydrochloride

Product 1

HCID 22794895N-acetyl-4-hydroxy-L-proline ethyl esterYield 165.3%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

345 g of acetic anhydride was added dropwise to a suspension of 600 g of 4-hydroxy-L-proline ethyl ester hydrochloride, 683 g of triethylamine and 2.4 L of chloroform at not higher than 10° C. while cooling. After stirring for 2 hours, water (0.6 L) was added, and the layers were separated. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure to obtain 1020 g of N-acetyl-4-hydroxy-L-proline ethyl ester as an oil.

Workup

  1. temperaturewhile cooling
  2. customthe layers were separated
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f3f465efaca547fe8bd1b575fb3e8787
Source dataset
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07485665B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes