(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 1418974Notes

Reaction equation

HRID 1418974 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 methoxycarbonylsulphamoyltriethylammonium 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-186652c58fde4dcdaee7d014a8db5faa
Source dataset
uspto-grants-1999_03
Patent number
US05885986

Reaction notes

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