Hydrochloric Acid → HCID 70051023, compound

HRID 266486Notes

Reaction equation

HRID 266486 reaction equation
[C:1]1([N:7]2[C:11]([S:12][CH2:13][N:14]3[C:24](=[O:25])[C:23]4[C:18](=[C:19]([O:29][CH2:30][C:31]([O:33]C(C)(C)C)=[O:32])[CH:20]=[CH:21][C:22]=4[O:26][CH2:27][CH3:28])[S:15]3(=[O:17])=[O:16])=[N:10][N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>FC(F)(F)C(O)=O.ClCCl.CC(C)=O>[C:1]1([N:7]2[C:11]([S:12][CH2:13][N:14]3[C:24](=[O:25])[C:23]4[C:18](=[C:19]([O:29][CH2:30][C:31]([OH:33])=[O:32])[CH:20]=[CH:21][C:22]=4[O:26][CH2:27][CH3:28])[S:15]3(=[O:17])=[O:16])=[N:10][N:9]=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 70052380HCID 70052380, compound

Product 1

HCID 70051023HCID 70051023, compoundYield 17%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 6344DichloromethaneSolvent2×HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2-(1-phenyltetrazol-5-yl)thiomethyl-4-ethoxy-7-(t-butoxycarbonylmethoxy)saccharin (Example 52, 0.47 g) in trifluoroacetic acid (5-10 mL) and dichloromethane (5-10 mL) was stirred at room temperature for two hours, then stripped of volatiles, then stripped three times more from dichloromethane, then stripped once more from acetone. A solution of the residual oil in acetone (1 mL) was added to ice-water (100 mL) containing concentrated hydrochloric acid (1 mL). The resulting solid was collected, washed with water and dried (0.34 g). A solution thereof in dichloromethane was eluted through silica gel in a 15-mL sintered glass funnel with chloroform-methanol (95:5) affording 2-(1-phenyltetrazol-5-yl)thiomethyl-4-ethoxy-7-carboxymethoxysaccharin, 70 mg, 17% yield, mp 187°-189° C.

Workup

  1. customThe resulting solid was collected
  2. washwashed with water
  3. customdried (0.34 g)
  4. washA solution thereof in dichloromethane was eluted through silica gel in a 15-mL sintered glass funnel with chloroform-methanol (95:5)

Sources & evidence

ORD record
ord-69aff9b0271244f4825088d3aff7494f
Source dataset
uspto-grants-1997_07
Patent number
US05650422

Reaction notes

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