Tetrahydrofuran → HCID 54216162, compound

HRID 1606963Notes

Reaction equation

HRID 1606963 reaction equation
[NH2-].[Na+].[Cl:3][C:4]1[C:9]2[C:10](=[O:22])[N:11]3[CH2:21][CH2:20][C@H:12]3[C:13]3[N:14]([CH:15]=[N:16][C:17]=3[CH:18]=O)[C:8]=2[CH:7]=[CH:6][CH:5]=1.O1CCC[CH2:24]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:3][C:4]1[C:9]2[C:10](=[O:22])[N:11]3[CH2:21][CH2:20][C@H:12]3[C:13]3[N:14]([CH:15]=[N:16][C:17]=3[CH:18]=[CH2:24])[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24533Sodium amideHCID 53858665HCID 53858665, compound

Product 1

HCID 54216162HCID 54216162, compound

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

8.70 g of an equimolar mixture of methyltriphenylphosphonium bromide and sodium amide were stirred for 20 minutes in 60 ml of tetrahydrofuran. 6 g (20 mmol) of (S)-8-chloro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxaldehyde was then added portionwise thereto and the mixture was stirred for a further 1 hour. The mixture was subsequently filtered and the filtrate was evaporated. After chromatography of the residue on silica gel while eluting with cyclohexane/ether/isopropanol (3:3:1) and subsequent recrystallization from ethyl acetate there was obtained (S)-8-chloro-12,12a-dihydro-1-vinyl-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one of melting point 171°-172°.

Workup

  1. filtrationThe mixture was subsequently filtered
  2. customthe filtrate was evaporated
  3. washAfter chromatography of the residue on silica gel while eluting with cyclohexane/ether/isopropanol (3:3:1) and subsequent recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-ea64017955cc4542973d571e79be6728
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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