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

HRID 1195127Notes

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]

Participants

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

waitat ambient temperature for 18 hours
filtrationthe mixture filtered
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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