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Dicyclohexylcarbodiimide → [Nalpha-t-Butoxycarbonyl-beta-(4-thiazolyl) alanyl]-glycine t-butyl ester

HRID 1195127
Notes
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Reaction equation

HRID 1195127 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([O:20][C:21]([NH:23][C@H:24]([C:31]([OH:33])=O)[CH2:25][C:26]1[N:27]=[CH:28][S:29][CH:30]=1)=[O:22])([CH3:19])([CH3:18])[CH3:17].[C:34]([O:38][C:39](=[O:42])[CH2:40][NH2:41])([CH3:37])([CH3:36])[CH3:35]>C(OCC)(=O)C.C(O)(=O)C>[C:34]([O:38][C:39](=[O:42])[CH2:40][NH:41][C:31](=[O:33])[C@H:24]([CH2:25][C:26]1[N:27]=[CH:28][S:29][CH:30]=1)[NH:23][C:21]([O:20][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:22])([CH3:37])([CH3:36])[CH3:35]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 151417Glycine tert-butyl esterHCID 2734486(S)-2-((tert-Butoxycarbonyl)amino)-3-(thiazol-4-yl)propanoic acid

Product 1

HCID 53829975[Nalpha-t-Butoxycarbonyl-beta-(4-thiazolyl) alanyl]-glycine t-butyl esterYield 110.2%

Reagents, catalysts & solvents 2

HCID 176
Acetic Acid
Catalyst
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Dicyclohexyl carbodiimide (226 mg) was added to a solution of 273 mg of Nα -t-butoxycarbonyl-β-(4-thiazolyl)-L-alanine and 132 mg of glycine t-butylester in 5 ml of ethyl acetate at 0° C. The reaction solution was stirred at 0° C. for 0.5 hour, then at ambient temperature for 18 hours. 4 drops of glacial acetic acid was then added to the reaction mixture and the mixture filtered. The filtrate was concentrated under vacuum to provide 426 mg of the title compound as an oil.

Workup

  1. waitat ambient temperature for 18 hours
  2. filtrationthe mixture filtered
  3. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-c6e52115daf34ea7a66c1eae8ffb8c85
Source dataset
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05110799

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes