Benzenepropanoic acid → Benzenepentanoic acid

HRID 635209Notes

Reaction equation

HRID 635209 reaction equation
[C:1]1([C:7]2C=C[C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C=CC=CC(O)=O)C=CC=CC=1.C1(CCC(O)=O)C=CC=CC=1>>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 107Benzenepropanoic acidHCID 66724(1,1'-Biphenyl)-4-carboxylic acidHCID 737775-Phenyl-2,4-pentadienoic acid

Product 1

HCID 16757Benzenepentanoic acid

Procedure

The same procedure as in Example 31 was repeated except that 4-phenylbenzoic acid, 5-phenyl-2,4-pentadienoic acid and 3-phenylpropionic acid were used, respectively, in place of 5-phenylvaleric acid to obtain N-cyclopropylmethyl-7α-(4-phenylbenzoylamino)-6,14-endoethenotetrahydronorthebaine 41 (88%), N-cyclopropylmethyl-7α-(5-phenyl-2,4-bentadienoylamino)-6,14-endoethenotetrahydronorthebaine 42 (94%) and N-cyclopropylmethyl-7α-(3-phenylpropionylamino)-6,14-endoethenotetrahydronorthebaine 43 (84%), respectively.

Sources & evidence

ORD record
ord-0ab55340b4d249b7918210331825aa65
Source dataset
uspto-grants-2001_02
Patent number
US06187782B1

Reaction notes

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