Ethylmorpholine → HCID 69952840, compound

HRID 1979266Notes

Reaction equation

HRID 1979266 reaction equation
[C:1]([NH:9][CH2:10][CH2:11][C@@H:12]([C@@H:20]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:21]([NH:23][NH:24][CH2:25][CH:26]([CH3:28])[CH3:27])=[O:22])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.[N:34]1([CH2:39][C:40](O)=[O:41])[CH:38]=[CH:37][N:36]=[CH:35]1.C(N1CCOCC1)C.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(OCC)(=O)C>[C:1]([NH:9][CH2:10][CH2:11][C@@H:12]([C@@H:20]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:21]([NH:23][N:24]([C:40](=[O:41])[CH2:39][N:34]1[CH:38]=[CH:37][N:36]=[CH:35]1)[CH2:25][CH:26]([CH3:27])[CH3:28])=[O:22])[C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69951698HCID 69951698, compoundHCID 69953627HCID 69953627, compound

Product 1

HCID 69952840HCID 69952840, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.763 g of 2(R)-[3-benzamido-1(S)-(tert-butoxycarbonyl)propyl]-2′-isobutyl-4-methylvalerohydrazide and 0.780 g of 2-(1H-imidazol-1-yl)acetic acid hydrogen bromide in 8 ml of dimethylformamide was cooled to 0° C. under nitrogen and treated with 0.45 ml of N-ethylmorpholine and 0.720 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride. The mixture was allowed to warm to room temperature and stirred overnight. Evaporation of the solvent gave a residue which was dissolved in ethyl acetate and washed with water and saturated aqueous sodium chloride. Drying over anhydrous magnesium sulfate, filtration, and evaporation gave 0.914 g of 2(R)-[3-benzamido-1(S)-(tert-butoxycarbonyl)propyl]-2′-[2-(1H-imidazol-1-yl)acetyl]-2′-isobutyl-4-methylvalerohydrazide in the form of an off-white foam.

Workup

  1. customEvaporation of the solvent
  2. customgave a residue which
  3. washwashed with water and saturated aqueous sodium chloride
  4. dry with materialDrying over anhydrous magnesium sulfate, filtration, and evaporation

Sources & evidence

ORD record
ord-c7672abad57e436b8749b2cdcc76c9f5
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

Loading…