(Methoxycarbonylsulfamoyl)triethylammonium hydroxide → methyl (S)-2-(5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a]thieno[2,3-f][1,4]-diazepin-3-yl)-4,5-dihydro-oxazole-4-carboxylate

HRID 1737394Notes

Reaction equation

HRID 1737394 reaction equation
O[CH2:2][C@H:3]([NH:8][C:9]([C:11]1[N:12]=[CH:13][N:14]2[C:20]3[CH:21]=[CH:22][S:23][C:19]=3[C:18](=[O:24])[N:17]([CH3:25])[CH2:16][C:15]=12)=[O:10])[C:4]([O:6][CH3:7])=[O:5].[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O>O1CCCC1>[CH3:25][N:17]1[C:18](=[O:24])[C:19]2[S:23][CH:22]=[CH:21][C:20]=2[N:14]2[CH:13]=[N:12][C:11]([C:9]3[O:10][CH2:2][C@@H:3]([C:4]([O:6][CH3:7])=[O:5])[N:8]=3)=[C:15]2[CH2:16]1

Participants

4

Reactant 2

HCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxideHCID 53755917methyl (S)-3-hydroxy-2-(5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a]thieno[2,3-f][1,4]-diazepin-3-ylcarbonylamino)-propionate

Product 1

HCID 54314375methyl (S)-2-(5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a]thieno[2,3-f][1,4]-diazepin-3-yl)-4,5-dihydro-oxazole-4-carboxylateYield 22.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 13.7 g (0.0377 mol) of methyl (S)-3-hydroxy-2-(5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepin-3-ylcarbonylamino)-propionate in 270 ml of tetrahydrofuran was treated while gassing with argon with 9.87 g (0.0414 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 2 hrs. and completely freed from the solvents. The residue was partitioned between water and dichloromethane, extracted, chromatographed over silica gel with ethyl acetate as the eluent and recrystallized from acetonitrile. There were obtained 2.94 g (22%) of methyl (S)-2-(5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepin-3-yl)-4,5-dihydro-oxazole-4-carboxylate as white crystals; m.p. 215-217°. [α]D20 =+41.2° (CHCl3, c=1%). A further 3.25 g (25%) of yellowish crystals were recovered from the mother liquor.

Workup

  1. temperatureat reflux for 2 hrs
  2. customThe residue was partitioned between water and dichloromethane
  3. extractionextracted
  4. customchromatographed over silica gel with ethyl acetate as the eluent
  5. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-05bad90336114af6914b087d214ef082
Source dataset
uspto-grants-1999_10
Patent number
US05962450

Reaction notes

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