Sulfuric Acid → (R)-2-(3,5-dibromo-4-hydroxy-phenyl)-1-methoxycarbonyl-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

HRID 1725750Notes

Reaction equation

HRID 1725750 reaction equation
OS(O)(=O)=O.[O:6]=[C:7]1[N:13]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C@@H:23](OC)[C:24](=C=O)[C:25]3[CH:30]=[C:29]([Br:31])[C:28]([O:32]COCC[Si](C)(C)C)=[C:27]([Br:41])[CH:26]=3)=[O:21])[CH2:16][CH2:15]2)[CH2:12][CH2:11][C:10]2[CH:46]=[CH:47][CH:48]=[CH:49][C:9]=2[NH:8]1>C1COCC1.CO>[O:6]=[C:7]1[N:13]([CH:14]2[CH2:15][CH2:16][N:17]([C:20]([O:22][C@@H:23]([C:20]([O:22][CH3:23])=[O:21])[CH2:24][C:25]3[CH:26]=[C:27]([Br:41])[C:28]([OH:32])=[C:29]([Br:31])[CH:30]=3)=[O:21])[CH2:18][CH2:19]2)[CH2:12][CH2:11][C:10]2[CH:46]=[CH:47][CH:48]=[CH:49][C:9]=2[NH:8]1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 86608969(R)-2-[3,5-dibromo-4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-1-methoxy-carbonyl-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

Product 1

HCID 67302314(R)-2-(3,5-dibromo-4-hydroxy-phenyl)-1-methoxycarbonyl-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere 5.46 mL methanolic H2SO4 (0.5 M) were added to a solution of 4.30 g (5.69 mmol) of (R)-2-[3,5-dibromo-4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-1-methoxy-carbonyl-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate in 40 mL THF and 40 mL MeOH and the reaction solution was stirred for 6 h at RT. The reaction mixture was evaporated down i.vac and the residue was reacted further without purification.

Workup

  1. customThe reaction mixture was evaporated down i.vac
  2. customthe residue was reacted further without purification

Sources & evidence

ORD record
ord-1db0d73c82104c1698ae1342d729a47c
Source dataset
uspto-grants-2009_02
Patent number
US07491717B2

Reaction notes

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