Water → HCID 178501108, compound

HRID 538070Notes

Reaction equation

HRID 538070 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][N:12]2[C:18](=[O:19])[CH2:17][C:16]3[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=3[NH:14][C:13]2=[O:24])[CH2:7][CH2:6]1)=[O:4].[C:25]([O-])([O-])=O.[K+].[K+].CI.O>CN(C=O)C>[CH3:1][O:2][C:3]([C@H:5]1[CH2:6][CH2:7][C@H:8]([CH2:11][N:12]2[C:18](=[O:19])[CH2:17][C:16]3[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=3[N:14]([CH3:25])[C:13]2=[O:24])[CH2:9][CH2:10]1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178501107HCID 178501107, compound

Product 1

HCID 178501108HCID 178501108, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of trans-4-(2,4-Dioxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-ylmethyl)-cyclohexanecarboxylic acid methyl ester (1 mmol, 0.35 g) in DMF dry (6 mL) under argon was sequentially added K2CO3 (1.6 mmol, 0.22 g) and MeI (2.2 mmol, 140 μL). The mixture was stirred at room temperature overnight. Then H2O (10 mL) was added and the solution was loaded on a C18 cartridge, wash with water (3×5 mL) and then the desired product was eluted with MeOH. The solvent was removed under reduced pressure to give the pure titled compound (0.29 g, yield 80%).

Workup

  1. washwash with water (3×5 mL)
  2. washthe desired product was eluted with MeOH
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2dbb394bad3248abbe2e4a45866a3ba1
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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