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 641255Notes

Reaction equation

HRID 641255 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-b6660a262c794f02aa6c3fe12973b793
Source dataset
uspto-grants-2010_04
Patent number
US07696196B2

Reaction notes

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