1,2-Dichloroethane → N-(2(S)-ACETYLTHIOMETHYL-3-(2-METHYLPHENYL)-PROPANOYL)-alpha-PHENYL-beta-ALANINE ETHYL ESTER

HRID 1587986Notes

Reaction equation

HRID 1587986 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:15])[CH:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:7][NH2:8])[CH3:3].[C:16]([S:19][CH2:20][C@@H:21]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH3:32])[C:22](O)=[O:23])(=[O:18])[CH3:17].C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.C(Cl)CCl>CN(C=O)C>[CH2:2]([O:4][C:5](=[O:15])[CH:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:7][NH:8][C:22](=[O:23])[C@@H:21]([CH2:20][S:19][C:16](=[O:18])[CH3:17])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH3:32])[CH3:3]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 15915818Ethyl 3-amino-2-phenylpropanoate hydrochlorideHCID 228417862(S)-acetylthiomethyl-3-(2-methylphenyl)propionic acid

Product 1

HCID 86746978N-(2(S)-ACETYLTHIOMETHYL-3-(2-METHYLPHENYL)-PROPANOYL)-alpha-PHENYL-beta-ALANINE ETHYL ESTER

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine α-phenyl-β-alanine ethyl ester, hydrochloride (0.40 g, 1.7 mmol) with 2(S)-acetylthiomethyl-3-(2-methylphenyl)propionic acid (0.44 g, 1.77 mmol), HOBT (0.26 g, 1.7 mmol) and triethylamine (0.25 g, 2.6 mmol) in 15 ml DMF. Add EDC (0.32 g, 1.7 mmol), stir 18 hr., partion with EtOAc-water, and wash with 1N HCl, then NaHCO3. Chromatograph on silica, eluting with 1:1 Et2O-hexane, to obtain the title compound, a 1:1 mixture of diastereomers, as an oil, [α]D26 =-19.9° (EtOH).

Workup

  1. wash, partion with EtOAc-water, and wash with 1N HCl
  2. washChromatograph on silica, eluting with 1:1 Et2O-hexane

Sources & evidence

ORD record
ord-f729b0ddb8e94a06861b2b9f3478b943
Source dataset
uspto-grants-1993_06
Patent number
US05219886

Reaction notes

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