Dicyclohexylcarbodiimide → 6-(4'-octylbiphenylcarbonyloxy)-1,2,3,4-tetrahydro-2-naphthalenecarboxylic acid (R)-1-methylheptyl ester

HRID 1419

Reaction equation

HRID 1419 reaction equation
[CH3:1][C@@H:2]([O:9][C:10]([CH:12]1[CH2:21][CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([OH:22])[CH:18]=2)[CH2:13]1)=[O:11])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].FC(F)(F)[C@H:25]([OH:32])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].[CH2:35]([C:43]1[CH:48]=[CH:47][C:46](C2C=CC(C(O)=O)=CC=2)=[CH:45][CH:44]=1)[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH3:1][C@@H:2]([O:9][C:10]([CH:12]1[CH2:21][CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][C:25]([C:26]3[C:27]([C:46]4[CH:45]=[CH:44][C:43]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])=[CH:48][CH:47]=4)=[CH:28][CH:29]=[CH:30][CH:31]=3)=[O:32])[CH:18]=2)[CH2:13]1)=[O:11])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 1714884AC55649HCID 2779099(R)-(+)-1,1,1-Trifluoro-2-octanolHCID 543109351,2,3,4-tetrahydro-6-hydroxynaphthalene-2-carboxylic acid (R)-1-methylheptyl ester

Product 1

HCID 545089106-(4'-octylbiphenylcarbonyloxy)-1,2,3,4-tetrahydro-2-naphthalenecarboxylic acid (R)-1-methylheptyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 0.31 g (1 mmol) of 1,2,3,4-tetrahydro-6-hydroxynaphthalene-2-carboxylic acid (R)-1-methylheptyl ester obtained as in the fourth stage of Example 23 where R-1-methyl heputanol was used in stead of (R)-1-trifluoromethylheptanol, 0.31 g (1 mmol) of 4'-octylbiphenyl-4-carboxylic acid (FK-1124-8 from Teikoku Kagaku Sangyo K.K.), 0.02 g (0.16 mmol) of 4-N,N-dimethylaminopyridine and 15 ml of methylene chloride was added dropwise 3 ml of a methylene chloride solution containing 0.27 g (1.3 mmol) of N,N'-dicyclohexylcarbodiimide with stirring at room temperature over a period of 3 hours.

Workup

  1. customobtained as in the fourth stage of Example 23 where R-1-methyl heputanol

Sources & evidence

ORD record
ord-a8ec9300a50c487a97fd5c9549637998
Source dataset
uspto-grants-1998_03
Patent number
US05725798

Linked notes

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