Hydrochloric Acid → HCID 54549745, compound

HRID 440198Notes

Reaction equation

HRID 440198 reaction equation
C(N(CCCC)[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH2:23][CH2:24][CH2:25][O:26]C3CCCOC3)(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[CH:8][CH:7]=1)CCC.Cl.[O:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1>>[CH2:39]([O:38][C:6]1[CH:7]=[CH:8][C:9]([CH:12]=[CH:13][C:14]2[CH:15]=[CH:16][C:17]([S:20]([CH2:23][CH2:24][CH2:25][OH:26])(=[O:21])=[O:22])=[CH:18][CH:19]=2)=[CH:10][CH:11]=1)[CH2:40][CH2:41][CH2:42][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:9][CH2:8][CH2:7][CH2:6][CH2:11][CH3:10]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 53735611HCID 53735611, compound

Product 1

HCID 54549745HCID 54549745, compound

Conditions

Temperature
50 °C

Procedure

9.02 g (13.8 mmol) of 3i are dissolved in 140 ml of tetrahydrofuran. After addition of 100 ml of 2M hydrochloric acid the mixture is heated at 50° C. for 4 hours. The mixture becomes turbid and on cooling a colorless precipitate separates, which is filtered off and first washed with a little THF and then with water. The solid is dried in a vacuum desiccator. 4.50 g of colorless powder of m.p. 137° C. are obtained. The mother liquor is concentrated, extracted a number of times with dichloromethane, the extracts are dried with magnesium sulfate, the solvent distilled off and the resulting oily residue is chromatographed with isohexane/acetic ester mixtures on a silica gel column. A total of 5.90 g (75%) of product are isolated.

Workup

  1. temperatureon cooling a colorless precipitate separates, which
  2. filtrationis filtered off
  3. washfirst washed with a little THF
  4. customThe solid is dried in a vacuum desiccator

Sources & evidence

ORD record
ord-6bcb712ef73c4210acce0feba6c95d03
Source dataset
uspto-grants-1996_05
Patent number
US05517350

Reaction notes

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