Methanol → 2-Benzo[1,3]dioxol-5-ylmethyl-4-(benzo[1,3]dioxol-5-ylsulfanyl)-1,1-dioxo-1,2-dihydro-1lambda6-benzo[e][1,2]thiazine-3-carboxylic acid

HRID 1449546Notes

Reaction equation

HRID 1449546 reaction equation
C[O:2][C:3]([C:5]1[N:6]([CH2:27][C:28]2[CH:36]=[CH:35][C:31]3[O:32][CH2:33][O:34][C:30]=3[CH:29]=2)[S:7](=[O:26])(=[O:25])[C:8]2[CH:24]=[CH:23][CH:22]=[CH:21][C:9]=2[C:10]=1[S:11][C:12]1[CH:20]=[CH:19][C:15]2[O:16][CH2:17][O:18][C:14]=2[CH:13]=1)=[O:4].CO.[Li+].[OH-]>C1COCC1.O.Cl>[O:32]1[C:31]2[CH:35]=[CH:36][C:28]([CH2:27][N:6]3[C:5]([C:3]([OH:4])=[O:2])=[C:10]([S:11][C:12]4[CH:20]=[CH:19][C:15]5[O:16][CH2:17][O:18][C:14]=5[CH:13]=4)[C:9]4[CH:21]=[CH:22][CH:23]=[CH:24][C:8]=4[S:7]3(=[O:26])=[O:25])=[CH:29][C:30]=2[O:34][CH2:33]1

Participants

7

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 543966672-Benzo[1,3]dioxol-5-ylmethyl-4-(benzo[1,3]dioxol-5-ylsulfanyl)-1,1-dioxo-1,2-dihydro-1lambda6-benzo[e][1,2]thiazine-3-carboxylic acid methyl ester

Product 1

HCID 442135452-Benzo[1,3]dioxol-5-ylmethyl-4-(benzo[1,3]dioxol-5-ylsulfanyl)-1,1-dioxo-1,2-dihydro-1lambda6-benzo[e][1,2]thiazine-3-carboxylic acidYield 88%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To 2-benzo[1,3]dioxol-5-ylmethyl-4-(benzo[1,3]dioxol-5-ylsulfanyl)-1,1-dioxo-1,2-dihydro-1λ6 -benzo[e][1,2]thiazine-3-carboxylic acid methyl ester (0.467 g, 0.89 mmol) in THF:methanol:water (5 mL:2 mL:2 mL) was added LiOH(0.46 g, 19 mmol). Stirred at room temperature for 5 hours, diluted with water (80 mL) and 50% HCl (10 mL) then extracted with chloroform (3×80 mL). Dried with magnesium sulfate and removed solvent to afford the title compound as a foam (0.4 g, 88%);

Workup

  1. extractionthen extracted with chloroform (3×80 mL)
  2. dry with materialDried with magnesium sulfate
  3. customremoved solvent

Sources & evidence

ORD record
ord-f586a2e7c0504c2b966dd93c652ec4ef
Source dataset
uspto-grants-1997_02
Patent number
US05599811

Reaction notes

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