Toluene → HCID 54339882, compound

HRID 1655738Notes

Reaction equation

HRID 1655738 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[C:25](Cl)(Cl)=[O:26].C1(C)C=CC=CC=1.[CH3:36][O:37][C:38](=[O:48])[C@H:39]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[NH2:40]>C(Cl)Cl.O>[CH3:36][O:37][C:38](=[O:48])[C@H:39]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[NH:40][C:25](=[O:26])[N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

8

Reactant 5

HCID 1140TolueneHCID 6371PhosgeneHCID 7656DibenzylamineHCID 81531DiisopropylethylamineHCID 736234L-Phenylalanine, methyl ester

Product 1

HCID 54339882HCID 54339882, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1 g (5.06 mmol) of dibenzylamine and 1.73 ml (10.1 mmol) of Hunig base in 50 ml of methylene chloride were treated dropwise while cooling with ice with 2.6 ml of phosgene in toluene (20%. 5.06 mmol) and the solution obtained was stirred at 0° for 3 hours. Then, 1.1 g of L-phenylalanine methyl ester were added and the mixture was heated to 40° for 12 hours. Thereafter, the reaction mixture was poured into water, extracted with methylene chloride and the extracts were dried over sodium sulfate. The solvent was then removed under reduced pressure and the residue was chromatographed on silica gel using a 15:1 mixture of methylene chloride and ether as the eluting agent, to obtain 900 mg (45%) of N-(dibenzylcarbamoyl)-3-phenyl-L-alanine methyl ester as a white solid. MS: 402 (M)+.

Workup

  1. customthe solution obtained
  2. temperaturethe mixture was heated to 40° for 12 hours
  3. extractionextracted with methylene chloride
  4. dry with materialthe extracts were dried over sodium sulfate
  5. customThe solvent was then removed under reduced pressure
  6. customthe residue was chromatographed on silica gel using
  7. additiona 15:1 mixture of methylene chloride and ether as the eluting agent

Sources & evidence

ORD record
ord-f018ea6f4ea7452fb1c77c50f614b91f
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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