Toluene → HCID 53790951, compound

HRID 1655740Notes

Reaction equation

HRID 1655740 reaction equation
[C:1](Cl)(Cl)=[O:2].C1(C)C=CC=CC=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.CC[N:20](C(C)C)C(C)C.Cl.[CH3:28][O:29][C:30](=[O:40])[C@H:31]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[NH2:32]>C(Cl)Cl>[CH3:28][O:29][C:30](=[O:40])[C@H:31]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[NH:32][C:1](=[O:2])[NH:20][N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

7

Reactant 5

HCID 1140TolueneHCID 6371PhosgeneHCID 8083MorpholineHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 81531Diisopropylethylamine

Product 1

HCID 53790951HCID 53790951, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.6 ml of phosgene in toluene (20%. 6.95 mmol) were added dropwise while cooling with ice to 0.6 ml (6.95 mmol) of morpholine and 2.4 ml (13.9 mmol) of Hunig base in 20 ml of methylene chloride, and the solution was stirred at 0° for 3 hours. Thereafter, 1.5 g (6.95 mmol) of phenylalanine methyl ester hydrochloride were added and the reaction solution was stirred at 40° for 12 hours. Subsequently, the reaction solution was poured onto ice and extracted with methylene chloride. The organic phase was dried over sodium sulfate and evaporated under reduced pressure. Chromatography of the residue on silica gel using a 2:1 mixture of methylene chloride and ether as the eluting agent yielded 400 mg (20%) of N-(morpholino-carbamoyl)-3-phenyl-L-alanine methyl ester in the form of a resin. MS: 292 (M)+.

Workup

  1. stirringthe reaction solution was stirred at 40° for 12 hours
  2. additionSubsequently, the reaction solution was poured onto ice
  3. extractionextracted with methylene chloride
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. customevaporated under reduced pressure
  6. additionChromatography of the residue on silica gel using a 2:1 mixture of methylene chloride and ether as the eluting agent

Sources & evidence

ORD record
ord-fa2cf4833b5f48a49ca15548dceadfab
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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