Sodium Hydroxide → 9-Iodo-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

HRID 532873Notes

Reaction equation

HRID 532873 reaction equation
C(OC([NH:8][CH2:9][C:10]([N:12]1[CH2:21][CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2[I:22])[CH:13]1[CH2:23][C:24]([O-:26])=O)=[O:11])=O)(C)(C)C.[Na+].C(OC(NCC(N1CCC2C(=CC=CC=2I)C1CC(OCC)=O)=O)=O)(C)(C)C.[OH-].[Na+]>CCO>[I:22][C:18]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:19]=1[CH2:20][CH2:21][N:12]1[C:10](=[O:11])[CH2:9][NH:8][C:24](=[O:26])[CH:23]=[C:13]12

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 86711322Sodium 2-(2-(2-((tert-butoxycarbonyl)amino)acetyl)-5-iodo-1,2,3,4-tetrahydroisoquinolin-1-yl)acetateHCID 86711324Ethyl 2-(2-(2-((tert-butoxycarbonyl)amino)acetyl)-5-iodo-1,2,3,4-tetrahydroisoquinolin-1-yl)acetate

Product 1

HCID 867113799-Iodo-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

sodium 2-(2-(2-((tert-butoxycarbonyl)amino)acetyl)-5-iodo-1,2,3,4-tetrahydroisoquinolin-1-yl)acetate. To an orange solution of ethyl 2-(2-(2-((tert-butoxycarbonyl)amino)acetyl)-5-iodo-1,2,3,4-tetrahydroisoquinolin-1-yl)acetate (57.4 mmol, 114 mmol) in EtOH (800 mL) was added an aqueous solution of NaOH (4M, 33 mL, 132 mmol) and the mixture was stirred at RT for 60 h. The mixture was then filtered and the filter cake was washed with Et2O. The filtrate was then concentrated down in vacuo until the formation of another precipitate. The mixture was then filtered again and the filter cake washed with Et2O. The combined filter cakes were then dried in vacuo to give the title compound (49.8 g) as a beige powder that was used as it is in the next step. UPLC-MS: MS 475.2 (M+H+); UPLC rt 1.00 min.

Workup

  1. filtrationThe mixture was then filtered
  2. washthe filter cake was washed with Et2O
  3. concentrationThe filtrate was then concentrated down in vacuo until the formation of another precipitate
  4. filtrationThe mixture was then filtered again
  5. washthe filter cake washed with Et2O
  6. filtrationThe combined filter cakes
  7. customwere then dried in vacuo

Sources & evidence

ORD record
ord-4a9aa1786417455fbb602268b142ff81
Source dataset
uspto-grants-2014_10
Patent number
US08853203B2

Reaction notes

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