Dimethylformamide → HCID 131716295, compound

HRID 330621Notes

Reaction equation

HRID 330621 reaction equation
[C:1]([NH:11][C@H:12]([C:20]([NH:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[N:29]=[CH:28][CH:27]=[CH:26]2)=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH2:33]([Br:36])[CH:34]=[CH2:35].CN(C)C=O>CCOCC>[Br-:36].[CH2:35]([N:29]1[C:30]2[C:25](=[CH:24][C:23]([NH:22][C:20](=[O:21])[C@H:12]([CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:11][C:1]([O:3][CH2:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[O:2])=[CH:32][CH:31]=2)[CH:26]=[CH:27][CH2:28]1)[CH:34]=[CH2:33]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 14310112HCID 14310112, compound

Product 1

HCID 131716295HCID 131716295, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution consisting of 100 mg (0.235 mmol) of 6-(N-carbobenzoxy-L-phenylalanylamino)quinoline (Brynes, et al., 1981), 204 1 of allyl bromide, and 0.5 ml of dimethylformamide was allowed to react at room temperature for 48 h and at 50° C. for 12 h. Crude product was isolated by precipitation with ether followed by two ether washes. The compound was purified by dissolving the solid in water at 50° C., filtering the undissolved material and lyophilizing to obtain pure XVI. Recrystallization from ethanol/ethyl acetate yielded 50 mg (39% yield): mp 160° C. decomposes, 219° C. melts;Rf(E)=0.08. Fast atom bombardment mass spectrum of XVI: calculated for MW (466)+Br-. Found 466 (M=).

Workup

  1. customto react at room temperature for 48 h and at 50° C. for 12 h
  2. customThe compound was purified
  3. dissolutionby dissolving the solid in water at 50° C.
  4. filtrationfiltering the undissolved material

Sources & evidence

ORD record
ord-a311db44c77f4574bdb302a7a918f745
Source dataset
uspto-grants-1990_01
Patent number
US04897444

Reaction notes

Loading…