Hydrochloric Acid → HCID 22618814, compound

HRID 842269Notes

Reaction equation

HRID 842269 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][C:17]([NH:26]C(OC)=O)([CH2:23][CH2:24][CH3:25])[C:18](OCC)=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+].Cl.[OH-].[K+]>O1CCCC1.CO.O>[NH2:26][C:17]([CH2:16][CH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH2:23][CH2:24][CH3:25])[CH2:18][OH:19]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 4148881Lithium borohydrideHCID 22618711HCID 22618711, compound

Product 1

HCID 22618814HCID 22618814, compoundYield 63.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of ethyl 2-(2-(2-benzyloxyphenyl)ethyl)-2-methoxycarbonylaminopentanoate (2.3 g) in tetrahydrofuran (50 ml), under a nitrogen atmosphere, lithium borohydride (0.24 g) was added and the mixture was refluxed under heating for 2.5 hours. Then, a 2N dilute hydrochloric acid (5.5 ml) was added thereto and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated brine, dried over sodium sulfate and the solvent was distilled away under reduced pressure. The residue obtained was dissolved in methanol (30 ml), and tetrahydrofuran (1 ml) and a 5N aqueous potassium hydroxide solution (10 ml) were added thereto and the mixture was refluxed under heating for 4 days. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated brine, dried over sodium sulfate and the solvent was distilled away under reduced pressure. The reaction mixture was concentrated under reduced pressure to give the subject compound (1.1 g).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 2.5 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated brine
  5. dry with materialdried over sodium sulfate
  6. distillationthe solvent was distilled away under reduced pressure
  7. customThe residue obtained
  8. temperaturethe mixture was refluxed
  9. temperatureunder heating for 4 days
  10. extractionextracted with ethyl acetate
  11. washThe organic layer was washed with a saturated brine
  12. dry with materialdried over sodium sulfate
  13. distillationthe solvent was distilled away under reduced pressure
  14. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6b41f4064bc84609be7c07635219594d
Source dataset
uspto-grants-2002_04
Patent number
US06372800B1

Reaction notes

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