HCID 70050615, compound → HCID 70052380, compound

HRID 266485Notes

Reaction equation

HRID 266485 reaction equation
Cl[CH2:2][N:3]1[C:13](=[O:14])[C:12]2[C:7](=[C:8]([O:18][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:9]=[CH:10][C:11]=2[O:15][CH2:16][CH3:17])[S:4]1(=[O:6])=[O:5].[Na].[C:28]1([N:34]2[C:38]([SH:39])=[N:37][N:36]=[N:35]2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[C:28]1([N:34]2[C:38]([S:39][CH2:2][N:3]3[C:13](=[O:14])[C:12]4[C:7](=[C:8]([O:18][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:9]=[CH:10][C:11]=4[O:15][CH2:16][CH3:17])[S:4]3(=[O:6])=[O:5])=[N:37][N:36]=[N:35]2)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

3

Reactant 2

HCID 70050615HCID 70050615, compoundHCID 178527989HCID 178527989, compound

Product 1

HCID 70052380HCID 70052380, compoundYield 71%

Procedure

By the method of part F of Example 45 condensation of 2-chloromethyl-4-ethoxy-7-(t-butoxycarbonylmethoxy)saccharin (1.42 g) and 1-phenyltetrazol-5-thiol sodium salt (0.70 g initially and a small amount more after 6 hours reaction time, total reaction time 8 hours) and isolation of the product (1.20 g) by extraction with dichloromethane and purification of part (0.42 g) thereof by column chromatography on silica gel using dichloromethane-acetone (up to 98:2) as eluant afforded 2-(1-phenyltetrazol-5-yl)thiomethyl-4-ethoxy-7-(t-butoxycarbonylmethoxy)saccharin, 300 mg, 71% yield, mp 110°-112° C.

Workup

  1. extractionby extraction
  2. customwith dichloromethane and purification of part (0.42 g)

Sources & evidence

ORD record
ord-67ca169af7954544821a0b10e1a97c72
Source dataset
uspto-grants-1997_07
Patent number
US05650422

Reaction notes

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