Hydrochloric Acid → HCID 178517125, compound

HRID 538077Notes

Reaction equation

HRID 538077 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][N:12]2[CH2:18][CH2:17][C:16]3[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=3[NH:14][C:13]2=[O:23])[CH2:7][CH2:6]1)=[O:4].[Li+].[OH-].Cl>O1CCOCC1>[O:23]=[C:13]1[NH:14][C:15]2[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=2[CH2:17][CH2:18][N:12]1[CH2:11][C@H:8]1[CH2:9][CH2:10][C@H:5]([C:3]([OH:4])=[O:2])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 178501097HCID 178501097, compound

Product 1

HCID 178517125HCID 178517125, compoundYield 104.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of trans-4-(2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-ylmethyl)-cyclohexanecarboxylic acid methyl ester (0.3 g, 0.95 mmol) in dioxane (7 mL) at 0° C. was added a 2N solution of LiOH. The reaction mixture was stirred at 0° C. for 20 min, allowed to reach ambient temperature and stirred additionally for 2 h. Then a 1N solution of HCl was added until acid pH, and the mixture was extracted with EtOAc, The organic layer was dried over Na2SO4 and solvent removed under reduced pressure to afford the titled compound (0.3 g, 96%).

Workup

  1. customto reach ambient temperature
  2. stirringstirred additionally for 2 h
  3. extractionthe mixture was extracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4 and solvent
  5. customremoved under reduced pressure

Sources & evidence

ORD record
ord-78f75bbb70e146748809154e7eb32598
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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