Hydrochloric Acid → HCID 11381978, compound

HRID 989454Notes

Reaction equation

HRID 989454 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N-]C(C)C)(C)C.[Li+].Cl.O.[CH2:30]([Cl:32])[Cl:31]>O1CCCC1.CCCCCCC.C(C1C=CC=CC=1)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:17](=[O:19])[CH:30]([Cl:32])[Cl:31])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 6344DichloromethaneHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 2724682Lithium diisopropylamide

Product 1

HCID 11381978HCID 11381978, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 7500EthylbenzeneSolventHCID 8028TetrahydrofuranSolvent2×HCID 8900HeptaneSolvent

Procedure

Methyl ester (1.40 g) of N-tert-butoxycarbonyl-L-phenylalanine was dissolved in dehydrated tetrahydrofuran (27 ml) and methylene chloride (0.80 ml), and the obtained solution was cooled to −20° C. 2M solution (6.25 ml) of lithium diisopropylamide in heptane, tetrahydrofuran and ethylbenzene were added thereto, and they were stirred for 1 hour. 2 N Hydrochloric acid (12.5 ml) and water (12.5 ml) were added to the reaction mixture to terminate the reaction. The temperature was elevated to room temperature. After the extraction with ethyl acetate and water, the obtained solution in ethyl acetate was analyzed by HPLC to find that the intended (3S)-3-tert-butoxycarbonylamino-1,1-dichloro-4-phenyl-2-butanone (0.94 g) was obtained in a yield of 57%. The obtained solution in ethyl acetate was dried over anhydrous magnesium sulfate. Magnesium sulfate was filtered off. The solvent was evaporated under reduced pressure. Ethyl acetate was added to the residue to form a slurry. The crystals thus formed were separated from the slurry and dried to obtain the intended (3S)-3-tert-butoxycarbonylamino-1,1-dichloro-4-phenyl-2-butanone (0.77 g) in a yield of 46%.

Workup

  1. customto terminate
  2. customthe reaction
  3. customwas elevated to room temperature
  4. extractionAfter the extraction with ethyl acetate and water
  5. customwas obtained in a yield of 57%
  6. dry with materialThe obtained solution in ethyl acetate was dried over anhydrous magnesium sulfate
  7. filtrationMagnesium sulfate was filtered off
  8. customThe solvent was evaporated under reduced pressure
  9. additionEthyl acetate was added to the residue
  10. customto form a slurry
  11. customThe crystals thus formed
  12. customwere separated from the slurry
  13. customdried

Sources & evidence

ORD record
ord-015196da2e9b443c909406700e5d80ac
Source dataset
uspto-grants-2003_10
Patent number
US06639094B2

Reaction notes

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