(Methoxycarbonylsulfamoyl)triethylammonium hydroxide → HCID 54469685, compound

HRID 1737387Notes

Reaction equation

HRID 1737387 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:27])[N:9]([CH3:26])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([NH:18][C@@H:19]([CH2:24]O)[C:20]([O:22][CH3:23])=[O:21])=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O>O1CCCC1>[Cl:1][C:2]1[C:7]2[C:8](=[O:27])[N:9]([CH3:26])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[O:17][CH2:24][C@@H:19]([C:20]([O:22][CH3:23])=[O:21])[N:18]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxideHCID 53816448HCID 53816448, compound

Product 1

HCID 54469685HCID 54469685, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 14.0 g (0.0356 mol) of methyl (S)-2-(7-chloro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-3-ylcarbonylamino)-3-hydroxy-propionate in 250 ml of tetrahydrofuran was treated while gassing with argon with 9.3 g (0.0392 mol) of methoxycarbonylsulphamoyl-triethylammonium hydroxide internal salt (Burgess reagent) according to the method described in Tetr. Letters 1992, 33, 907. The mixture was boiled at reflux for 31/2 hrs. and completely freed from the solvents. The residue was partitioned between dichloromethane and water, extracted and chromatographed over silica gel with ethyl acetate/ethanol 19:1 as the eluent. There were obtained 6.80 g (51%) of methyl (S)-2-(7-chloro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-3-yl)-4,5-dihydro-oxazole-4-carboxylate as white crystals; m.p. 216-218°.

Workup

  1. temperatureat reflux for 31/2 hrs
  2. customThe residue was partitioned between dichloromethane and water
  3. extractionextracted
  4. customchromatographed over silica gel with ethyl acetate/ethanol 19:1 as the eluent

Sources & evidence

ORD record
ord-d66e43281b684baba708d336a16915ab
Source dataset
uspto-grants-1999_10
Patent number
US05962450

Reaction notes

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