Acetic Acid → HCID 178451477, compound

HRID 1443379Notes

Reaction equation

HRID 1443379 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:17]([C:18](=O)[NH:19][CH2:20][C:21](=O)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(O)=O.[OH-].[NH4+:35]>C(OCC)C>[C:1]([O:5][C:6]([N:8]1[CH:17]([C:18]2[NH:19][CH:20]=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:35]=2)[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14923Ammonium HydroxideHCID 235707253-(2-oxo-2-phenyl-ethylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert butyl ester

Product 1

HCID 178451477HCID 178451477, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The product prepared in Step A above (3.55 g, 9 mmol), NH4OAc (ammonium acetate) (20.8 g, 270 mmol) and AcOH (acetic acid) (30 mL) were combined at room temperature and the reaction mixture was warmed on a steam bath for about 3 hours. The reaction mixture was then cooled to room temperature and poured into an ice slurry mix (400 g). To this mixture was added concentrated ammonium hydroxide (50 mL) and ethyl ether. The layers were separated, and the aqueous phase washed with a second portion of ethyl ether. The organic phases were combined, dried over MgSO4, filtered, and concentrated under reduced pressure to yield a brown foam. This sample was purified by preparative HPLC to yield the purified title compound as a white powder. LC indicated the sample was 96% pure at 214 nm.

Workup

  1. customwere combined at room temperature
  2. temperaturethe reaction mixture was warmed on a steam bath for about 3 hours
  3. additionmix (400 g)
  4. customThe layers were separated
  5. washthe aqueous phase washed with a second portion of ethyl ether
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto yield a brown foam
  10. customThis sample was purified by preparative HPLC
  11. customto yield the
  12. custompurified title compound as a white powder

Sources & evidence

ORD record
ord-3cbd462d42b047bca53d3ddbbcda25b5
Source dataset
uspto-grants-2010_02
Patent number
US07659402B2

Reaction notes

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