Water → HCID 67346993, compound

HRID 2036884Notes

Reaction equation

HRID 2036884 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH2:10][N:9](CC1C=CC=CC=1)[CH2:8]2)=[O:4].C([O-])(O)=O.[Na+].[CH2:26]([O:33][C:34](Cl)=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH2:10][N:9]([C:34]([O:33][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:35])[CH2:8]2)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 516892Sodium Bicarbonate2×HCID 23301778Methyl 2-benzylisoindoline-5-carboxylate

Product 1

HCID 67346993HCID 67346993, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

2-Benzyl-2,3-dihydro-1H-isoindole-5-carboxylic acid methyl ester (3.9 g) and NaHCO3 (12.3 g) are suspended in CH2Cl2 (50 mL) and the mixture is treated with benzylchloroformate (Z—Cl) (10.8 mL). The mixture is warmed to 30° C. and after 10 min the reaction mixture is added to a mixture of water (150 mL) with NaHCO3 (12.3 g), the organic phase is separated, dried and evaporated. To the residue are added MeOH and the crystalline solid is collected and dried. 3.79 g of the title compound are obtained with MP 59-65° C.

Workup

  1. customthe organic phase is separated
  2. customdried
  3. customevaporated
  4. additionTo the residue are added MeOH
  5. customthe crystalline solid is collected
  6. customdried

Sources & evidence

ORD record
ord-e426318b8d7647b3964af5baf51ec485
Source dataset
uspto-grants-2013_11
Patent number
US08575193B2

Reaction notes

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