Hydrochloric Acid → HCID 20532139, compound

HRID 1759135Notes

Reaction equation

HRID 1759135 reaction equation
C[Al](C)C.C1(O)CCCC1.[CH3:11][C:12]1[C:17]2[CH2:18][CH2:19][CH2:20][C:16]=2[N:15]=[C:14]([NH:21][C:22]([NH:24][S:25]([C:28]2[CH:37]=[CH:36][CH:35]=[CH:34][C:29]=2[C:30]([O:32]C)=[O:31])(=[O:27])=[O:26])=[O:23])[N:13]=1.Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:11][C:12]1[C:17]2[CH2:18][CH2:19][CH2:20][C:16]=2[N:15]=[C:14]([NH:21][C:22]([NH:24][S:25]([C:28]2[CH:37]=[CH:36][CH:35]=[CH:34][C:29]=2[C:30]([OH:32])=[O:31])(=[O:27])=[O:26])=[O:23])[N:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7298CyclopentanolHCID 13068374HCID 13068374, compoundHCID 16682925Trimethylaluminum

Product 1

HCID 20532139HCID 20532139, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To 20 ml of dry toluene was added 2.4 ml of 2 M trimethylaluminum in toluene under a nitrogen atmosphere. Subsequently, 0.82 g cyclopentanol in 1 ml toluene was added via syringe and the mixture stirred at ambient temperature for 15 minutes. After addition of 1.56 g of methyl 2-[[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate to the mixture, the reaction was heated to 80° for 3.5 hours. The mixture was then cooled in ice while B 40 ml of 5% aqueous hydrochloric acid was added. Ethyl acetate was then added and shaking of the two phase mixture resulted in the crystallization of the product which was collected and dried to yield 1.5 g of 2-[[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, cyclopentyl, ester, m.p. 183°-184°. The product showed characteristic absorptions at 3120, 1725, 1720 cm-1 in the infrared spectrum and at 1.7-2.35, 2.50, 2.95, 5.4, 7.6, 8.4, 8.5 and 13.0 ppm in the nuclear magnetic resonance spectrum (60 MHz), indicating the title compound.

Workup

  1. temperaturethe reaction was heated to 80° for 3.5 hours
  2. additionwas added
  3. stirringshaking of the two phase mixture
  4. customresulted in the crystallization of the product which
  5. customwas collected
  6. customdried

Sources & evidence

ORD record
ord-cc9223670fe843f294fd4bb0d03a0834
Source dataset
uspto-grants-1982_07
Patent number
US04339267

Reaction notes

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