Acetic Anhydride → HCID 118939066, compound

HRID 524005Notes

Reaction equation

HRID 524005 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH2:7][CH2:8][N:9]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C@@H:22]([NH2:24])[CH3:23])=[CH:18][CH:17]=3)[CH2:10][C:11]=2[CH:12]=[CH:13][CH:14]=1)=[O:4].[C:25](OC(=O)C)(=[O:27])[CH3:26]>CC(O)=O>[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH2:7][CH2:8][N:9]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([C@@H:22]([NH:24][C:25](=[O:27])[CH3:26])[CH3:23])=[CH:20][CH:21]=3)[CH2:10][C:11]=2[CH:12]=[CH:13][CH:14]=1)=[O:4]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 118939071HCID 118939071, compound

Product 1

HCID 118939066HCID 118939066, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 475 mg (1.46 mmol) 2-[4-((S)-1-amino-ethyl)-benzyl]-1,2,3,4-tetrahydro-isoquinoline-5-carboxylic acid methyl ester (example XXXV) in 5 mL AcOH are added 152 μL (1.61 mmol) acetic anhydride and the mixture is stirred at r.t. over night. After that time, the reaction mixture is quenched by the addition of a sat. aq. NaHCO3 solution and extracted three times with EtOAc. The organic layers are combined, dried over MgSO4, filtered and the solvent is removed in vacuo.

Workup

  1. customAfter that time, the reaction mixture is quenched by the addition of a sat. aq. NaHCO3 solution
  2. extractionextracted three times with EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-1ca752a82d1e41bfbd61f7ff160593a7
Source dataset
uspto-grants-2016_05
Patent number
US09340510B2

Reaction notes

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