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4-Methylmorpholine → benzyloxycarbonyl-L-histidyl-glycine amide

HRID 892691
Notes
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Reaction equation

HRID 892691 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:19]([OH:21])=O)[CH2:13][C:14]1[N:18]=[CH:17][NH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.Cl.[NH2:30][CH2:31][C:32]([NH2:34])=[O:33].ClC(OCC(C)C)=O>O1CCCC1>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:19]([NH:30][CH2:31][C:32]([NH2:34])=[O:33])=[O:21])[CH2:13][C:14]1[N:18]=[CH:17][NH:16][CH:15]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 2723639Glycinamide hydrochlorideHCID 178523877HCID 178523877, compound

Product 1

HCID 178514040benzyloxycarbonyl-L-histidyl-glycine amide

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

Na -t-butyloxycarbonyl-Nim -benzyloxycarbonyl-L-histidine was dissolved in tetrahydrofuran (THF) and neutralized with one equivalent of N-methylmorpholine. It was then coupled with glycinamide hydrochloride using isobutyl chloroformate and N-methylmorpholine. After two hours at -20° C. and an additional hour at ambient temperature, the reaction was quenched with 2N aqueous potassium bicarbonate. This product was extracted into ethyl acetate, washed with 1M aqueous citric acid, and saturated sodium bicarbonate. The organic phase was dried over anhydrous sodium sulfate. Filtration and evaporation gave Na -t-butyloxycarbonyl-Nim -benzyloxycarbonyl-L-histidyl-glycine amide.

Workup

  1. customan additional hour at ambient temperature, the reaction was quenched with 2N aqueous potassium bicarbonate
  2. extractionThis product was extracted into ethyl acetate
  3. washwashed with 1M aqueous citric acid, and saturated sodium bicarbonate
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-d3d0f0ba26784da8bc79687d4d6c20f0
Source dataset
uspto-grants-1992_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05118665

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes