Ethylmorpholine → HCID 91594889, compound

HRID 1979219Notes

Reaction equation

HRID 1979219 reaction equation
[CH3:1][O:2][CH2:3][C:4]([OH:6])=O.C(N1CCOCC1)C.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.O1CCCCC1ONC([C@H]([C@@H:57]([CH2:66][CH:67]([CH3:69])[CH3:68])[C:58]([NH:60][NH:61][CH2:62][CH:63]([CH3:65])[CH3:64])=[O:59])C/C=C/C1C=CC=CC=1)=O>CN(C)C=O>[CH2:62]([N:61]([C:4](=[O:6])[CH2:3][O:2][CH3:1])[NH:60][C:58](=[O:59])[CH2:57][CH2:66][CH:67]([CH3:69])[CH3:68])[CH:63]([CH3:65])[CH3:64]

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 12251Methoxyacetic AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86756879(E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)-carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazide

Product 1

HCID 91594889HCID 91594889, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.180 g of methoxyacetic acid in 10 ml of dimethylformamide was treated in sequence with 0.254 ml of N-ethylmorpholine, 0.270 g of 1-hydroxybenzotriazole and 0.384 g of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride. Stirring was continued at room temperature for 1 hour and then 0.459 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl)-4-phenyl-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide was added. Stirring was continued at room temperature overnight and then the solvent was evaporated and replaced by ethyl acetate. The ethyl acetate layer was washed with 5% aqueous citric acid, 5% aqueous sodium hydrogen carbonate and brine and then dried over anhydrous magnesium sulphate. Evaporation and trituration with diethyl ether gave 0.543 g of (E)-2(R)-[1(S)-(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-2′-(2-methoxyacetyl)-4-methylvalerohydrazide in the form of a white solid.

Workup

  1. stirringStirring
  2. waitwas continued at room temperature overnight
  3. customthe solvent was evaporated
  4. washThe ethyl acetate layer was washed with 5% aqueous citric acid, 5% aqueous sodium hydrogen carbonate and brine
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customEvaporation and trituration with diethyl ether

Sources & evidence

ORD record
ord-6709474b15214f5792e42e8f32e5793b
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

Loading…