Ethylmorpholine → HCID 86756954, compound

HRID 1979245Notes

Reaction equation

HRID 1979245 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.[O:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[O:19][NH:20][C:21]([C@H:23]([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])[CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:22].C(N1CCOCC1)C.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(OCC)(=O)C>[O:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[O:19][NH:20][C:21]([C@H:23]([C@@H:33]([CH2:42][CH:43]([CH3:45])[CH3:44])[C:34]([NH:36][N:37]([C:10](=[O:12])[CH2:9][C:7]([N:2]1[CH:6]=[CH:5][N:4]=[CH:3]1)=[O:8])[CH2:38][CH:39]([CH3:41])[CH3:40])=[O:35])[CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:22]

Participants

7

Reactant 4

HCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69952674HCID 69952674, compoundHCID 86756955HCID 86756955, compound

Product 1

HCID 86756954HCID 86756954, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.415 g of 2-(1-imidazoyl)acetic acid hydrogen bromide and 0.461 g of 2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenylbutyl]-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. Drying over anhydrous magnesium sulphate, evaporation and trituration with diethyl ether followed by filtration and evaporation gave 0.340 g of 2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenylbutyl]-2′-[2-(1-imidazoyl)acetyl]-2′-isobutyl-4-methylvalerohydrazide in the form of a white solid.

Workup

  1. customEvaporation
  2. customgave a residue which
  3. washwashed with water and saturated aqueous sodium chloride solution
  4. dry with materialDrying over anhydrous magnesium sulphate, evaporation and trituration with diethyl ether
  5. filtrationfollowed by filtration and evaporation

Sources & evidence

ORD record
ord-412584e1e8b143c79adf7f0a7bad06ae
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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