Dicyclohexylcarbodiimide → (S)-alpha-cyano-3-phenoxybenzyl (R)-2-(4-trifluoromethylphenylamino)-3-methylbutanoate

HRID 443468Notes

Reaction equation

HRID 443468 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C@H:10]([CH:14]([CH3:16])[CH3:15])[C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1.[C:19]([C@@H:21](O)[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:23]=1)#[N:20].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[F:1][C:2]([F:17])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C@H:10]([CH:14]([CH3:16])[CH3:15])[C:11]([O:13][C@H:21]([C:19]#[N:20])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:23]=2)=[O:12])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 9837437(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrileHCID 13388455N-[4-(trifluoromethyl)phenyl]-D-valine

Product 1

HCID 13388459(S)-alpha-cyano-3-phenoxybenzyl (R)-2-(4-trifluoromethylphenylamino)-3-methylbutanoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

Following the procedure of Example 8, (R)-2-(4-trifluoromethylphenylamino)-3-methylbutanoic acid and (S)-α-cyano-3-phenoxybenzyl alcohol are combined, in the presence of 4-dimethylaminopyridine and dicyclohexylcarbodiimide, to yield (S)-α-cyano-3-phenoxybenzyl (R)-2-(4-trifluoromethylphenylamino)-3-methylbutanoate, specific rotation=+62.1° (c=9 mg/ml in CHCl3).

Sources & evidence

ORD record
ord-0b984214d07c4c3ea77a5a7accb41c30
Source dataset
uspto-grants-1981_04
Patent number
US04260633

Reaction notes

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