1,2-Dichloroethane → (+/-)-n-(4-Ethoxycarbonyl-3-phenylbutanoyl) serine methyl ester

HRID 989895Notes

Reaction equation

HRID 989895 reaction equation
[C:1]([CH2:4][CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])([OH:3])=O.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.C(Cl)CCl.Cl.[CH3:40][O:41][C:42](=[O:47])[C@H:43]([CH2:45][OH:46])[NH2:44]>CN(C=O)C>[CH3:40][O:41][C:42](=[O:47])[C@H:43]([CH2:45][OH:46])[NH:44][C:1](=[O:3])[CH2:4][CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 23389060Ethyl (+/-) 4-carboxy-3-phenylbutanoate

Product 1

HCID 53912906(+/-)-n-(4-Ethoxycarbonyl-3-phenylbutanoyl) serine methyl esterYield 67.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl (±) 4-carboxy-3-phenylbutanoate (1.00 g, 4.23 mmole) in dry DMF (20 mL) was added HOBt (686 mg, 5.08 mmole), Et3N (1.77 mL, 12.69 mmole), and EDC (974 mg, 5.08 mmole). After 30 min, L-serine methyl ester hydrochloride (790 mg, 5.08 mmole) was added. After 48 hr, the mixture was concentrated under reduced pressure. The residue was taken up in CH2Cl2 (50 mL) and washed sequentially with 20 mL each H2O, saturated NaHCO3, and H2O. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was chromatographed on silica gel (EtOAc) to give the title compound (961 mg, 67%) as a yellow oil: MS (ES) m/e 338 (M+H)+.

Workup

  1. waitAfter 48 hr
  2. concentrationthe mixture was concentrated under reduced pressure
  3. washwashed sequentially with 20 mL each H2O, saturated NaHCO3, and H2O
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on silica gel (EtOAc)

Sources & evidence

ORD record
ord-a19e0d5c09384f48b54b6f0a5aaf7d3d
Source dataset
uspto-grants-2002_10
Patent number
US06458814B1

Reaction notes

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