N,N-Dimethylglycine → HCID 86756903, compound

HRID 1979211Notes

Reaction equation

HRID 1979211 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][C:4](O)=[O:5].C(N1CCOCC1)C.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.O1CCCCC1ONC([C@H]([C@@H:58]([CH2:67][CH:68]([CH3:70])[CH3:69])[C:59]([NH:61][NH:62][CH2:63][CH:64]([CH3:66])[CH3:65])=[O:60])C/C=C/C1C=CC=CC=1)=O>CN(C)C=O.C(OCC)(=O)C>[CH2:63]([N:62]([C:4](=[O:5])[CH2:3][N:2]([CH3:7])[CH3:1])[NH:61][C:59](=[O:60])[CH2:58][CH2:67][CH:68]([CH3:70])[CH3:69])[CH:64]([CH3:66])[CH3:65]

Participants

8

Reactant 5

HCID 673N,N-DimethylglycineHCID 7525EthylmorpholineHCID 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 86756903HCID 86756903, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.155 g of N,N-dimethylglycine in 10 ml of dimethylformamide was treated in sequence with 0.167 ml of N-ethylmorpholine, 0.216 g of 1-hydroxybenzotriazole and 0.307 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride. Stirring was continued for 1 hour at room temperature 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 overnight and then the mixture was diluted with ethyl acetate and washed in sequence with 5% aqueous sodium hydrogen carbonate and brine. Drying over magnesium sulphate and evaporation gave 0.591 g of (E)-2(R)-[1(S)-(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-4-methyl-2′-[2-(dimethylamino)acetyl]valerohydrazide in the form of a white solid.

Workup

  1. stirringStirring
  2. waitwas continued overnight
  3. washwashed in sequence with 5% aqueous sodium hydrogen carbonate and brine
  4. dry with materialDrying over magnesium sulphate and evaporation

Sources & evidence

ORD record
ord-9de54524f78144e08ae0952a94019949
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

Loading…