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

HRID 1587986ノート

反応式

HRID 1587986 の反応式
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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-f729b0ddb8e94a06861b2b9f3478b943
出典データセット
uspto-grants-1993_06
特許番号
US05219886

反応ノート

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