Lithium Hydroxide → HCID 15952667, compound

HRID 2244271Notes

Reaction equation

HRID 2244271 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9]([C:11]2[N:20]3[C:14]([CH2:15][N:16]([C:25]([C:27]4[CH:36]=[CH:35][C:30]([C:31]([O:33]C)=[O:32])=[CH:29][CH:28]=4)=[O:26])[C:17]4[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=4[CH2:19]3)=[CH:13][CH:12]=2)=[O:10])[CH:2]=1.[OH-].[Li+]>CO.O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9]([C:11]2[N:20]3[C:14]([CH2:15][N:16]([C:25]([C:27]4[CH:28]=[CH:29][C:30]([C:31]([OH:33])=[O:32])=[CH:35][CH:36]=4)=[O:26])[C:17]4[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=4[CH2:19]3)=[CH:13][CH:12]=2)=[O:10])[CH:2]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68687909HCID 68687909, compound

Product 1

HCID 15952667HCID 15952667, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of methyl 4-{[3-{[(pyridin-3-ylmethyl)amino]carbonyl}-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-yl]carbonyl}benzoate of Example 87 (0.315 g, 0.656 mmol) in methanol (4 mL) and water (2 mL) was added lithium hydroxide (31.4 mg, 1.31 mmol) and the reaction mixture heated to reflux for 1 hour. The cooled reaction mixture was diluted with water (20 mL) and washed with ethyl acetate (2×20 mL). The aqueous phase was then acidified to pH 4.5 by the addition of 2 M hydrochloric acid and the resulting milky suspension allowed to stand at 4° C. for 16 hours. The solid product was filtered, washed with water, and dried at 50° C. in vacuo overnight to afford the title compound (0.271 g, 89%) as a white solid.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 1 hour
  3. customThe cooled reaction mixture
  4. washwashed with ethyl acetate (2×20 mL)
  5. additionThe aqueous phase was then acidified to pH 4.5 by the addition of 2 M hydrochloric acid
  6. filtrationThe solid product was filtered
  7. washwashed with water
  8. customdried at 50° C. in vacuo overnight

Sources & evidence

ORD record
ord-6c534065b294493f8009cdd4890e40b9
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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