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

HRID 1587986노트

반응식

HRID 1587986 반응식
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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-f729b0ddb8e94a06861b2b9f3478b943
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05219886

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