Hydrochloric Acid → HCID 12098836, compound

HRID 989458Notes

Reaction equation

HRID 989458 reaction equation
C([Li])CCC.[CH2:6]([Cl:8])[Cl:7].[CH2:9]([N:16]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C@H:17]([C:25](O)=[O:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl>CCCCCC.O1CCCC1.O>[Cl:7][CH:6]([Cl:8])[C:25](=[O:26])[C@@H:17]([N:16]([CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 10980880N,N-Dibenzyl-L-phenylalanineHCID 178418339Butyllithium

Product 1

HCID 12098836HCID 12098836, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

Dehydrated tetrahydrofuran (15 ml) was cooled to −78° C. 1.53 M solution (6.5 ml) of n-butyllithium in hexane and then a solution of methylene chloride (0.8 ml) in dehydrated tetrahydrofuran (5 ml) were added thereto, and they were stirred for 10 minutes. A solution of benzyl ester (2.18 g) of N,N-dibenzyl-L-phenylalanine in dehydrated tetrahydrofuran (7 ml) was added to the obtained mixture, and they were stirred for 1 hour. 2 N hydrochloric acid (15 ml) and water (15 ml) were added to the reaction mixture to terminate the reaction. The temperature was elevated to room temperature. After the addition of water followed by the extraction with ethyl acetate, the obtained solutions in ethyl acetate were combined together and dried over anhydrous magnesium sulfate. Magnesium sulfate was filtered out. The solvent was evaporated under reduced pressure to obtain the intended (3S)-1,1-dichloro-3-dibenzylamino-4-phenyl-2-butanone (2.04 g) in a yield of 99%.

Workup

  1. stirringwere stirred for 1 hour
  2. customto terminate
  3. customthe reaction
  4. customwas elevated to room temperature
  5. extractionfollowed by the extraction with ethyl acetate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationMagnesium sulfate was filtered out
  8. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f2421b823cac4d0cb2570336223206b1
Source dataset
uspto-grants-2003_10
Patent number
US06639094B2

Reaction notes

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