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 643098Notes

Reaction equation

HRID 643098 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-64611d2939b54fdd907d67cfa51c939a
Source dataset
uspto-grants-2010_04
Patent number
US07696209B2

Reaction notes

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