Triethylamine → HCID 66940370, compound

HRID 1910169Notes

Reaction equation

HRID 1910169 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][C:5](Cl)=[O:6].Cl.[CH3:9][O:10][C:11](=[O:21])[C@H:12]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH2:13].C(N(CC)CC)C>ClCCl>[CH3:9][O:10][C:11](=[O:21])[CH:12]([NH:13][C:5](=[O:6])[CH2:4][CH2:3][S:2][CH3:1])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 129214403-(Methylthio)propionyl Chloride

Product 1

HCID 66940370HCID 66940370, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.556 g (11 mmol) of 3-methylsulfanyl-propionyl chloride was added slowly to a mixture of 2.20 g (10 mmol) of phenylalanine methyl ester hydrochloride, 4.18 mL (30 mmol) of triethyl amine and 50 mL of dichloromethane and stirred at room temperature for 2 h. The reaction mixture was partitioned between DCM (50 mL) and saturated NaHCO3 solution (100 mL). The aqueous layer was separated and extracted again with dichloromethane (100 mL). The combined organic extracts were dried over sodium sulfate and evaporated. Purification by column chromatography on silica gel gave 2.574 g (92%) of 2-(3-methylsulfanyl-propionylamino)-3-phenyl-propionic acid methyl ester. LCMS: 282 (M+1)+.

Workup

  1. customThe reaction mixture was partitioned between DCM (50 mL) and saturated NaHCO3 solution (100 mL)
  2. customThe aqueous layer was separated
  3. extractionextracted again with dichloromethane (100 mL)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. customevaporated
  6. customPurification by column chromatography on silica gel

Sources & evidence

ORD record
ord-9c3792d5a8aa4773be374977fd9317bf
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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