Ethylmorpholine → HCID 69950498, compound

HRID 1979253Notes

Reaction equation

HRID 1979253 reaction equation
[CH:1]1([CH2:6][CH2:7][CH2:8][C@@H:9]([C@@H:17]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:18]([NH:20][NH:21][CH2:22][CH:23]([CH3:25])[CH3:24])=[O:19])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.Br.[N:31]1([C:36]([CH2:38][C:39](O)=[O:40])=[O:37])[CH:35]=[CH:34][N:33]=[CH:32]1.C(N1CCOCC1)C.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(OCC)C>[CH:1]1([CH2:6][CH2:7][CH2:8][C@@H:9]([C@@H:17]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:18]([NH:20][N:21]([CH2:22][CH:23]([CH3:24])[CH3:25])[C:39](=[O:40])[CH2:38][C:36]([N:31]2[CH:35]=[CH:34][N:33]=[CH:32]2)=[O:37])=[O:19])[C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69952674HCID 69952674, compoundHCID 69953393HCID 69953393, compound

Product 1

HCID 69950498HCID 69950498, compoundYield 37.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 0.510 g of 2(R)-[4-cyclopentyl-1(S)-(tert-butoxycarbonyl)-butyl]-2′-isobutyl-4-methylvalerohydrazide in 10 ml of dimethylformamide was treated in sequence with 0.308 g of 2-(1-imidazoyl)acetic acid hydrogen bromide, 0.172 g of N-ethylmorpholine and 0.286 g of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride and then stirred overnight at room temperature. The mixture was diluted with diethyl ether and washed with water and saturated aqueous sodium chloride solution. Drying over anhydrous magnesium sulphate and evaporation gave a residue which was purified by column chromatography on silica gel, using ethyl acetate/hexane (1:3) and then dichloromethane/methanol (3:1) for the elution, to give 0.255 g of 2(R)-[4-cyclopentyl-1(S)-(tert-butoxycarbonyl)-butyl]-2′-isobutyl-2′-[2-(1-imidazoyl)acetyl]-4-methylvalerohydrazide in the form of a yellow oil.

Workup

  1. washwashed with water and saturated aqueous sodium chloride solution
  2. dry with materialDrying over anhydrous magnesium sulphate and evaporation
  3. customgave a residue which
  4. customwas purified by column chromatography on silica gel
  5. washdichloromethane/methanol (3:1) for the elution

Sources & evidence

ORD record
ord-598bee38b4bb46d092bec7b64c750f05
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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