Ethylmorpholine → HCID 86756915, compound

HRID 1979218Notes

Reaction equation

HRID 1979218 reaction equation
Br.[N:2]1([CH2:7][C:8]([OH:10])=O)[CH2:6][CH2:5][CH2:4][CH2:3]1.C(N1CCOCC1)C.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[O:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH:42]1[O:47][NH:48][C:49]([C@H:51]([C@@H:61]([CH2:70][CH:71]([CH3:73])[CH3:72])[C:62]([NH:64][NH:65][CH2:66][CH:67]([CH3:69])[CH3:68])=[O:63])[CH2:52]/[CH:53]=[CH:54]/[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)=[O:50]>CN(C)C=O>[O:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH:42]1[O:47][NH:48][C:49]([C@H:51]([C@@:61]([C:8](=[O:10])[CH2:7][N:2]1[CH2:3][CH2:4][CH2:5][CH2:6]1)([CH2:70][CH:71]([CH3:73])[CH3:72])[C:62]([NH:64][NH:65][CH2:66][CH:67]([CH3:68])[CH3:69])=[O:63])[CH2:52]/[CH:53]=[CH:54]/[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)=[O:50]

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69953295HCID 69953295, compoundHCID 86756879(E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)-carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazide

Product 1

HCID 86756915HCID 86756915, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.309 g of 2-(1-pyrrolidinyl)acetic acid hydrogen bromide in 20 ml of dimethylformamide was treated in sequence with 0.324 ml of N-ethylmorpholine, 0.212 g of 1-hydroxybenzotriazole and 0.301 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride. Stirring was continued at room temperature and for 1 hour then 0.450 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 at room temperature and then the solvent was evaporated and replaced by ethyl acetate. The ethyl acetate phase was washed with 5% aqueous sodium hydrogen carbonate and brine and then dried over anhydrous magnesium sulphate. Evaporation and trituration of the residue with diethyl ether gave 0.363 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-4-methyl-2-[2-(1-pyrrolidinyl)acetyl]valerohydrazide in the form of a white solid.

Workup

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

Sources & evidence

ORD record
ord-6e7db36cb5aa4021bafc8ca9a5827830
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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