Hydrochloric Acid → HCID 53906369, compound

HRID 1154469Notes

Reaction equation

HRID 1154469 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]3[CH2:23][CH2:22][CH2:21][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:25]1(O)[CH2:31][CH2:30]CC[CH2:27][CH2:26]1.Cl>CCO.CCO.CCO.CCO.[Ti]>[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]3[CH2:23][CH2:22][CH2:21][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([O:18][CH:19]3[CH2:30][CH2:31][CH2:25][CH2:26][CH2:27][CH2:20]3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10399CycloheptanolHCID 53890667ethyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]-benzodiazepine-1-carboxylate

Product 1

HCID 53906369HCID 53906369, compound

Reagents, catalysts & solvents 1

HCID 2724286Titanium(IV)ethoxideCatalyst

Procedure

A mixture of 10.35 g (30 mmol) of ethyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate, 50 g of cycloheptanol and 2 g of tetraethyl orthotitanate is heated to 130° for 8 hours, evaporated in vacuo, the residue is taken up in chloroform and the solution obtained is poured into about 20 percent hydrochloric acid. The mixture is stirred for 15 minutes, the chloroform phase is separated, washed successively with 2N hydrochloric acid and saturated sodium bicarbonate solution, dried over magnesium sulphate and evaporated. By crystallization from ethyl acetate/hexane there is obtained cycloheptyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate of melting point 179°-180°.

Workup

  1. temperatureis heated to 130° for 8 hours
  2. customevaporated in vacuo
  3. customthe solution obtained
  4. customthe chloroform phase is separated
  5. washwashed successively with 2N hydrochloric acid and saturated sodium bicarbonate solution
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customBy crystallization from ethyl acetate/hexane there

Sources & evidence

ORD record
ord-3e7dcc174c5848d2be55f45fa82f19b0
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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