Hydrochloric Acid → HCID 20561638, compound

HRID 1155275Notes

Reaction equation

HRID 1155275 reaction equation
[C:1]([CH2:5][N:6]1[C:11](=[O:12])[C:10]([N:13]2[C:17](=[O:18])[C:16]3=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]3[C:14]2=[O:23])=[CH:9][S:8][CH2:7]1)([O:3]C)=[O:2].O1CCCC1.Cl>O>[C:1]([CH2:5][N:6]1[C:11](=[O:12])[C:10]([N:13]2[C:14](=[O:23])[C:15]3=[CH:22][CH:21]=[CH:20][CH:19]=[C:16]3[C:17]2=[O:18])=[CH:9][S:8][CH2:7]1)([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 20561639HCID 20561639, compound

Product 1

HCID 20561638HCID 20561638, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 24 mg. (0.07 mmole) sample of the methyl ester product obtained in Step A. above, in a solution of 1.5 ml. of tetrahydrofuran, 0.5 ml. of water, and 0.25 ml. of concentrated hydrochloric acid, was refluxed under nitrogen for 3.5 hrs. The solution was cooled and diluted with 5 ml. of water and then extracted four times with a total of 15 ml. of dichloromethane. The organic phase was dried over sodium sulfate and concentrated in vacuo. The resulting residue was triturated with dichloromethane and crystals formed, which were washed with dichloromethane and dried to give 10.1 mg. of product having a m.p. of 227°-228° C. The mother liquor on concentration in vacuo also crystallized to give 13.3 mg. of product.

Workup

  1. temperatureThe solution was cooled
  2. additiondiluted with 5 ml
  3. extractionof water and then extracted four times with a total of 15 ml
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was triturated with dichloromethane and crystals
  7. customformed
  8. washwhich were washed with dichloromethane
  9. customdried
  10. customto give 10.1 mg
  11. concentrationThe mother liquor on concentration in vacuo
  12. customalso crystallized
  13. customto give 13.3 mg

Sources & evidence

ORD record
ord-6c91ad10bf22405f90e7799e4ebe8b48
Source dataset
uspto-grants-1981_11
Patent number
US04301151

Reaction notes

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