Sodium Hydroxide → trans-[(7-Chloro-1,2,3,4,10,14b-hexahydro-10-methyldibenzo[b,f]pyrido[1,2-d][1,4]diazepin-1-yl)amino]acetic Acid

HRID 16187Notes

Reaction equation

HRID 16187 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]([CH3:26])[C:7]3[CH:25]=[CH:24][CH:23]=[CH:22][C:8]=3[C@@H:9]3[C@H:14]([NH:15][CH2:16][C:17]([O:19]CC)=[O:18])[CH2:13][CH2:12][CH2:11][N:10]3[C:4]=2[CH:3]=1.[OH-].[Na+]>O1CCOCC1.O>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]([CH3:26])[C:7]3[CH:25]=[CH:24][CH:23]=[CH:22][C:8]=3[C@@H:9]3[C@H:14]([NH:15][CH2:16][C:17]([OH:19])=[O:18])[CH2:13][CH2:12][CH2:11][N:10]3[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86599896Ethyl trans-[(7-chloro-1,2,3,4,10,14b-hexahydro-10-methyldibenzo[b,f]pyrido[1,2-d][1,4]diazepin-1-yl)amino]acetate

Product 1

HCID 86599898trans-[(7-Chloro-1,2,3,4,10,14b-hexahydro-10-methyldibenzo[b,f]pyrido[1,2-d][1,4]diazepin-1-yl)amino]acetic AcidYield 12%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of ethyl trans-[(7-chloro-1,2,3,4,10,14b-hexahydro-10-methyldibenzo[b,f]pyrido[1,2-d][1,4]diazepin-1-yl)amino]acetate (35 mg, 0.09 mmol) in dioxane (1 mL) was added 4N (aq) NaOH (250 ul). The reaction mixture was stirred at 65° C. for 1.5 h. It was diluted with water (25 mL) whereafter the pH was adjusted to pH 2 with 2N (aq) HCL. The mixture was extracted with ethyl acetate (2×), washed with water and brine, dried (MgSO4) and evaporated. The crude product was purified with LC-MS to afford the title compound (4 mg, 12%). Data (m/z)=372 (M+H)+.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (2×)
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude product was purified with LC-MS

Sources & evidence

ORD record
ord-61bddab8e22e4eacae7133c9fc982f5a
Source dataset
uspto-grants-2010_06
Patent number
US07737136B2

Reaction notes

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