Sodium Hydroxide → HCID 118939113, compound

HRID 524006Notes

Reaction equation

HRID 524006 reaction equation
C[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]([NH:24][C:25](=[O:27])[CH3:26])[CH3:23])=[CH:18][CH:17]=3)[CH2:10][C:11]=2[CH:12]=[CH:13][CH:14]=1)=[O:4].[OH-].[Na+]>CO>[C:25]([NH:24][C@H:22]([C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:9]2[CH2:8][CH2:7][C:6]3[C:5]([C:3]([OH:4])=[O:2])=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:10]2)=[CH:17][CH:18]=1)[CH3:23])(=[O:27])[CH3:26]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118939066HCID 118939066, compound

Product 1

HCID 118939113HCID 118939113, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To 560 mg (1.53 mmol) 2-[4-((S)-1-acetylamino-ethyl)-benzyl]-1,2,3,4-tetrahydro-isoquinoline-5-carboxylic acid methyl ester (example XXXVI) in 5 mL MeOH are added 1.68 mL (1.68 mmol) aq. NaOH solution (c=1 mol/L). The reaction mixture is stirred for 1 h at 70° C. After that time, the solvent is partially removed in vacuo and the residue is extracted with DCM. The aq. layer is separated, alkalized with aq. HCl solution (c=1 mol/L) and extracted with EtOAc. The aq. layer was separated and the solvent was removed by lyophilization.

Workup

  1. customAfter that time, the solvent is partially removed in vacuo
  2. extractionthe residue is extracted with DCM
  3. customThe aq. layer is separated
  4. extractionextracted with EtOAc
  5. customThe aq. layer was separated
  6. customthe solvent was removed by lyophilization

Sources & evidence

ORD record
ord-6b860869686948f8be5de01b0d3e0bb8
Source dataset
uspto-grants-2016_05
Patent number
US09340510B2

Reaction notes

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