Hydrochloric Acid → 1-[(S)-6-bromo-5-(o-chlorophenyl)-2,3-dihydro-1,3-dimethyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-3-(2,3-dihydroxypropyl)urea

HRID 1632176Notes

Reaction equation

HRID 1632176 reaction equation
[Br:1][C:2]1[C:7]2[C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])=[N:9][C@@H:10]([CH3:15])[C:11](=[O:14])[N:12]([CH3:13])[C:6]=2[CH:5]=[CH:4][C:3]=1[NH:23][C:24]([NH:26][CH2:27][CH:28]1[CH2:32][O:31]C(C)(C)[O:29]1)=[O:25].Cl>C(O)C>[Br:1][C:2]1[C:7]2[C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])=[N:9][C@@H:10]([CH3:15])[C:11](=[O:14])[N:12]([CH3:13])[C:6]=2[CH:5]=[CH:4][C:3]=1[NH:23][C:24]([NH:26][CH2:27][CH:28]([OH:29])[CH2:32][OH:31])=[O:25]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 543347131-[(S)-6-bromo-5-(o-chlorophenyl)-2,3-dihydro-1,3-dimethyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-3-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]urea

Product 1

HCID 541193171-[(S)-6-bromo-5-(o-chlorophenyl)-2,3-dihydro-1,3-dimethyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-3-(2,3-dihydroxypropyl)urea

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-[(S)-6-bromo-5-(o-chlorophenyl)-2,3-dihydro-1,3-dimethyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-3-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]urea in ethanol is stirred at room temperature for 5 hours with 1N hydrochloric acid. The mixture is extracted with ethyl acetate, washed with water, dried over sodium sulphate and evaporated. The residue is chromatographed on silica gel while eluting with ethyl acetate/methanol (95:5). After recrystallization from methanol/ether, there is obtained 1-[(S)-6-bromo-5-(o-chlorophenyl)-2,3-dihydro-1,3-dimethyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-3-(2,3-dihydroxypropyl)urea of melting point 175° (decomposition).

Workup

  1. extractionThe mixture is extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customThe residue is chromatographed on silica gel
  6. washwhile eluting with ethyl acetate/methanol (95:5)
  7. customAfter recrystallization from methanol/ether

Sources & evidence

ORD record
ord-bb78981432d34c2b9a2efde104742cd9
Source dataset
uspto-grants-1984_10
Patent number
US04474777

Reaction notes

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