Ethylmorpholine → HCID 86756958, compound

HRID 1979248Notes

Reaction equation

HRID 1979248 reaction equation
Br.[N:2]1([C:7]([CH2:9][C:10]([OH:12])=O)=[O:8])[CH:6]=[CH:5][N:4]=[CH:3]1.[CH:13]1([CH2:19][CH2:20][CH2:21][C@@H:22]([C@@H:33]([CH2:42][CH:43]([CH3:45])[CH3:44])[C:34]([NH:36][NH:37][CH2:38][CH:39]([CH3:41])[CH3:40])=[O:35])[C:23](=[O:32])[NH:24][O:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(N1CCOCC1)C.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(OCC)(=O)C>[CH:13]1([CH2:19][CH2:20][CH2:21][C@@H:22]([C@@H:33]([CH2:42][CH:43]([CH3:45])[CH3:44])[C:34]([NH:36][N:37]([CH2:38][CH:39]([CH3:41])[CH3:40])[C:10](=[O:12])[CH2:9][C:7]([N:2]2[CH:6]=[CH:5][N:4]=[CH:3]2)=[O:8])=[O:35])[C:23](=[O:32])[NH:24][O:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

7

Reactant 4

HCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69952674HCID 69952674, compoundHCID 86756959HCID 86756959, compound

Product 1

HCID 86756958HCID 86756958, compoundYield 35.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.429 g of 2-(1-imidazoyl)acetic acid hydrogen bromide and 0.467 g of 2(R)-[4-Cyclohexyl-1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]butyl]-2′-isobutyl-4-methylvalerohydrazide in 5 ml of dimethylformamide was treated with 0.230 g of N-ethylmorpholine and 0.422 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and the mixture stirred overnight at room temperature. Evaporation gave a residue which was dissolved in ethyl acetate and washed with water and saturated aqueous sodium chloride solution then dried over anhydrous magnesium sulfate and evaporated. Purification by flash column chromatography on silica gel using methanol/dichloromethane (5:95) as the eluant gave 0.213 g of 2(R)-[4-cyclohexyl-1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]butyl]-2′-isobutyl-4-methyl-2′-[2-(1-imidazoyl)acetyl]valerohydrazide in the form of a white foam.

Workup

  1. customEvaporation
  2. customgave a residue which
  3. washwashed with water and saturated aqueous sodium chloride solution
  4. dry with materialthen dried over anhydrous magnesium sulfate
  5. customevaporated
  6. customPurification by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-490685493fec452db459b37cad874457
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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