Acetonitrile → (S)-3-Cyclohexyl-2-(1-oxoisoindolin-2-yl)propanoic acid

HRID 1018821Notes

Reaction equation

HRID 1018821 reaction equation
[OH2:1].[NH2:2][C@@H:3]([CH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)[C:4]([OH:6])=[O:5].[C:14](#N)[CH3:15]>>[CH:8]1([CH2:7][C@H:3]([N:2]2[CH2:15][C:14]3[C:9](=[CH:8][CH:7]=[CH:3][CH:4]=3)[C:10]2=[O:1])[C:4]([OH:6])=[O:5])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 16211120(S)-2-Amino-3-cyclohexylpropanoic acid hydrate

Product 1

HCID 1477119(S)-3-Cyclohexyl-2-(1-oxoisoindolin-2-yl)propanoic acidYield 78%

Procedure

A mixture of (S)-(+)-α-aminocyclohexanepropionic acid hydrate (5.00 g; 29.2 mmol) and phthalic dicarboxaldehyde (4.21 g; 31.3 mmol) in acetonitrile (120 mL) was refluxed for 20 h under nitrogen. The mixture was allowed to cool to room temperature and further cooled to 0° C. The solid was filtered off and washed once with cold acetonitrile (50 mL) to give 6.54 g (78%) of (S)-3-Cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid as a white solid: EI-HRMS m/e calcd for C17H21NO3 (M+) 287.1521, found 287.1521.

Workup

  1. temperaturewas refluxed for 20 h under nitrogen
  2. temperaturefurther cooled to 0° C
  3. filtrationThe solid was filtered off
  4. washwashed once with cold acetonitrile (50 mL)

Sources & evidence

ORD record
ord-8d899a94e18d41b3a929a0bea5b9579a
Source dataset
uspto-grants-2002_11
Patent number
US06482951B2

Reaction notes

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