Hydrochloric Acid → (R)-1-carboxy-2-(2-dimethylamino-7-methyl-1H-benzimidazol-5-yl)-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

HRID 491109Notes

Reaction equation

HRID 491109 reaction equation
[Li+].[OH-].[O:3]=[C:4]1[N:10]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C@@H:20]([C:35]([O:37]C)=[O:36])[CH2:21][C:22]3[CH:33]=[C:32]([CH3:34])[C:25]4[NH:26][C:27]([N:29]([CH3:31])[CH3:30])=[N:28][C:24]=4[CH:23]=3)=[O:18])[CH2:13][CH2:12]2)[CH2:9][CH2:8][C:7]2[CH:39]=[CH:40][CH:41]=[CH:42][C:6]=2[NH:5]1.Cl>O.C1COCC1>[O:3]=[C:4]1[N:10]([CH:11]2[CH2:12][CH2:13][N:14]([C:17]([O:19][C@@H:20]([C:35]([OH:37])=[O:36])[CH2:21][C:22]3[CH:33]=[C:32]([CH3:34])[C:25]4[NH:26][C:27]([N:29]([CH3:31])[CH3:30])=[N:28][C:24]=4[CH:23]=3)=[O:18])[CH2:15][CH2:16]2)[CH2:9][CH2:8][C:7]2[CH:39]=[CH:40][CH:41]=[CH:42][C:6]=2[NH:5]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 178501365HCID 178501365, compound

Product 1

HCID 178425373(R)-1-carboxy-2-(2-dimethylamino-7-methyl-1H-benzimidazol-5-yl)-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 9.0 mg (0.38 mmol) LiOH in 0.5 mL water was added to a solution of 80 mg (0.15 mmol) (R)-2-(2-dimethylamino-7-methyl-1H-benzimidazol-5-yl)-1-methoxycarbonyl-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate in 4 mL THF and the reaction mixture was stirred for 4 h at RT. 100 μL of 4 M HCl was added, the mixture was evaporated down i.vac. and the crude product was dried and then further reacted without purification.

Workup

  1. customthe mixture was evaporated down i.vac
  2. dry with materialand the crude product was dried
  3. customfurther reacted without purification

Sources & evidence

ORD record
ord-a5ba2befa2244252b21b88d770afa41e
Source dataset
uspto-grants-2009_05
Patent number
US07528129B2

Reaction notes

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