Hydrogen Bromide → HCID 20077376, compound

HRID 1655010Notes

Reaction equation

HRID 1655010 reaction equation
[CH:1]1([C:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]([CH2:16][CH2:17][CH3:18])[C:8](=[O:19])[CH:7]([NH:20]C(OCC3C=CC=CC=3)=O)[N:6]=2)[CH2:4][CH2:3][CH2:2]1.Br.C(OCC)C>C(O)(=O)C>[NH2:20][CH:7]1[N:6]=[C:5]([CH:1]2[CH2:2][CH2:3][CH2:4]2)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([CH2:16][CH2:17][CH3:18])[C:8]1=[O:19]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 20077364HCID 20077364, compound

Product 1

HCID 20077376HCID 20077376, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Cyclobutyl-1,3-dihydro-3(R,S)-[(benzyloxycarbonyl)amino]-1-propyl-2H-1,4-benzodiazepin-2-one (1.5 g, 3.7 mmol) was treated with a solution of 30% hydrogen bromide in acetic acid (5 ml), and stirred for 20 min at room temperature. The mixture was then added dropwise onto cold (0° C.) diethyl ether (50 ml). A white solid was precipitated and filtered off. The solid was treated with 10% sodium hydroxide solution (50 ml), then extracted with ethyl acetate (80 ml). The organic layer was separated, dried (Na2SO4) and evaporated to give a colourless oil. This material was then used without further purification.

Workup

  1. customA white solid was precipitated
  2. filtrationfiltered off
  3. additionThe solid was treated with 10% sodium hydroxide solution (50 ml)
  4. extractionextracted with ethyl acetate (80 ml)
  5. customThe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customto give a colourless oil
  9. customThis material was then used without further purification

Sources & evidence

ORD record
ord-48df6e5fef7844aa9d4e449f867015af
Source dataset
uspto-grants-1995_04
Patent number
US05410049

Reaction notes

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