Dichloromethane → HCID 15547332, compound

HRID 989456Notes

Reaction equation

HRID 989456 reaction equation
C([Li])CCC.[CH2:6]([Cl:8])[Cl:7].[C:9]1([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[N:16][C@H:17]([C:25](O)=[O:26])[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl-].[NH4+]>CCCCCC.O1CCCC1.C(OCC)C.O>[Cl:7][CH:6]([Cl:8])[C:25](=[O:26])[C@@H:17]([N:16]=[C:15]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 57425272HCID 57425272, compoundHCID 178418339Butyllithium

Product 1

HCID 15547332HCID 15547332, compoundYield 96%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A mixed solution of dehydrated tetrahydrofuran (6.2 ml) and diethyl ether (3.1 ml) was cooled to −78° C. 1.53 M solution (3.3 ml) of n-butyllithium in hexane and then a solution of methylene chloride (0.40 ml) in dehydrated tetrahydrofuran (3.3 ml) were added to the mixed solution and they were stirred for 10 minutes. Then a solution of methyl ester of N-(diphenylmethylene)-L-phenylalanine (0.86 g) in diethyl ether (3.3 ml) was added to the obtained solution. They were stirred for 2 hours. Saturated aqueous ammonium chloride solution was added to the reaction solution to terminate the reaction. The temperature was elevated to room temperature. After the addition of water followed by the extraction with ethyl acetate twice, the obtained solutions in ethyl acetate were combined together and washed with saturated aqueous sodium chloride6solution. The obtained solution in ethyl acetate solvent was 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-(diphenylmethylene) amino-4-phenyl-2-butanone (0.95 g) in a yield of 96%.

Workup

  1. stirringThey were stirred for 2 hours
  2. customto terminate
  3. customthe reaction
  4. customwas elevated to room temperature
  5. extractionfollowed by the extraction with ethyl acetate twice
  6. washwashed with saturated aqueous sodium chloride6solution
  7. dry with materialThe obtained solution in ethyl acetate solvent was dried over anhydrous magnesium sulfate
  8. filtrationMagnesium sulfate was filtered out
  9. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6476ce5f62a645a7a63afffbcf030cee
Source dataset
uspto-grants-2003_10
Patent number
US06639094B2

Reaction notes

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