L-Valine → m-Phenoxybenzyl 2-(5-methoxy-2-isoindolinyl)-3-methylbutanoate

HRID 1447952Notes

Reaction equation

HRID 1447952 reaction equation
BrCC1C=CC=C(C(F)(F)F)C=1CBr.N[C@H]([C:20](O)=[O:21])C(C)C.FC(F)(F)[C:25]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:26]=1[CH2:27][N:28]([CH:34]([CH:38]([CH3:40])[CH3:39])[C:35]([OH:37])=[O:36])[CH2:29]2.S(O[CH:48](C#N)[C:49]1[CH:54]=[CH:53][CH:52]=[C:51]([O:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[CH:50]=1)(=O)(=O)C>>[CH3:20][O:21][C:32]1[CH:31]=[C:30]2[C:26](=[CH:25][CH:33]=1)[CH2:27][N:28]([CH:34]([CH:38]([CH3:39])[CH3:40])[C:35]([O:37][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[C:51]([O:55][C:56]3[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=3)[CH:50]=1)=[O:36])[CH2:29]2

Participants

5

Reactant 4

HCID 6287L-ValineHCID 203828461,2-Bis(bromomethyl)-3-trifluoromethylbenzeneHCID 203828572-(4-Trifluoromethyl-2-isoindolinyl)-3-methylbutanoic acidHCID 20482835alpha-Cyano-m-phenoxybenzyl mesylate

Product 1

HCID 20382850m-Phenoxybenzyl 2-(5-methoxy-2-isoindolinyl)-3-methylbutanoate

Procedure

The α-cyano-m-phenoxybenzyl esters of the above are prepared using the procedure of Example 10 by reacting, e.g. 1,2-bis(bromomethyl)-3-trifluoromethylbenzene with valine to prepare 2-(4-trifluoromethyl-2-isoindolinyl)-3-methylbutanoic acid and esterifying using α-cyano-m-phenoxybenzyl mesylate.

Sources & evidence

ORD record
ord-cd888855f248413e852abb099127bdc7
Source dataset
uspto-grants-1979_12
Patent number
US04178293

Reaction notes

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