Hydrogen Bromide → HCID 18957787, compound

HRID 2379365Notes

Reaction equation

HRID 2379365 reaction equation
[CH:1]1([C:6]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]([CH3:17])[C:9](=[O:18])[CH:8]([NH:19]C(OCC3C=CC=CC=3)=O)[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Br.C(OCC)C>C(O)(=O)C>[NH2:19][CH:8]1[N:7]=[C:6]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH3:17])[C:9]1=[O:18]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 18957774HCID 18957774, compound

Product 1

HCID 18957787HCID 18957787, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 5-cyclopentyl-1,3-dihydro-1-methyl-3(R,S)-[(benzyloxycarbonyl)amino]-2H-1,4-benzodiazepin-2-one (475 mg, 1.2 mmol) was added 45% hydrobromic acid in acetic acid (1 ml) and the mixture stirred at room temperature for 2 h. Anhydrous diethyl ether (50 ml) was added and the resultant cream coloured suspension stirred at 0° C. for 1 h. On settling, the solvent was decanted off, and the solid triturated in anhydrous diethyl ether. The resultant solid was collected by filtration and washed with more diethyl ether. The solid was partitioned between 10% Na2CO3 solution (25 ml) and ethyl acetate (20 ml), the aqueous layer was further extracted with ethyl acetate (4×10 ml) and the organic extracts combined, dried (MgSO4), and evaporated to give the title compound (247 mg, 79%) as a colourless off.

Workup

  1. stirringstirred at 0° C. for 1 h
  2. customthe solvent was decanted off
  3. customthe solid triturated in anhydrous diethyl ether
  4. filtrationThe resultant solid was collected by filtration
  5. washwashed with more diethyl ether
  6. customThe solid was partitioned between 10% Na2CO3 solution (25 ml) and ethyl acetate (20 ml)
  7. extractionthe aqueous layer was further extracted with ethyl acetate (4×10 ml)
  8. dry with materialdried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-d3791e53314740ed9e0615a94acf694d
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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