Ethylmorpholine → HCID 69951698, compound

HRID 1979265Notes

Reaction equation

HRID 1979265 reaction equation
[C:1]([NH:9][CH2:10][CH2:11][C@@H:12]([C@@H:20]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:21]([OH:23])=O)[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.C(N1CCOCC1)C.O.OC1C2N=NNC=2C=CC=1.Cl.C(N=C=NCCCN(C)C)C.[CH2:59]([NH:63][NH2:64])[CH:60]([CH3:62])[CH3:61]>ClCCl>[C:1]([NH:9][CH2:10][CH2:11][C@@H:12]([C@@H:20]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:21]([NH:64][NH:63][CH2:59][CH:60]([CH3:62])[CH3:61])=[O:23])[C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 542420IsobutylhydrazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 20658017HCID 20658017, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 69951698HCID 69951698, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 0.78 g of 2(R)-[3-benzamido-1(S)-(tert-butoxycarbonyl)propyl]-4-methylvaleric acid in 10 ml of dichloromethane was cooled to 0° C. under nitrogen and treated sequentially with 0.80 ml of N-ethylmorpholine, 0.437 g of hydroxybenzotriazole hydrate, and 0.50 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride. The mixture was stirred for 5 minutes at 0° C. and then 1.1 g of isobutyl hydrazine was added. Stirring was continued overnight at room temperature and then the solvent was evaporated. The residue was dissolved in ethyl acetate and washed with 5% aqueous sodium hydrogen carbonate, water, 2M aqueous hydrogen chloride, and saturated aqueous sodium chloride. Drying over anhydrous magnesium sulfate, filtration and evaporation of the solvent gave 0.763 g of 2(R)-[3-benzamido-1(S)-(tert-butoxycarbonyl)propyl]-2′-isobutyl-4-methylvalerohydrazide in the form of an off-white foam.

Workup

  1. stirringStirring
  2. waitwas continued overnight at room temperature
  3. customthe solvent was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with 5% aqueous sodium hydrogen carbonate, water, 2M aqueous hydrogen chloride, and saturated aqueous sodium chloride
  6. dry with materialDrying over anhydrous magnesium sulfate, filtration and evaporation of the solvent

Sources & evidence

ORD record
ord-32d2f0e0f28448e2ae5355ed0be9eb44
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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