Diisopropylethylamine → 3-biphenyl-4-yl-2(S)-{[5-(3-trifluoromethoxy-phenoxymethyl)-pyrazine-2-carbonyl]-amino}-propionic acid methyl ester

HRID 2373854

反応式

HRID 2373854 の反応式
[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][CH:20]=1)[O:7][CH2:8][C:9]1[N:10]=[CH:11][C:12]([C:15]([OH:17])=O)=[N:13][CH:14]=1.Cl.[CH3:24][O:25][C:26](=[O:42])[C@@H:27]([NH2:41])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:31][CH:30]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>>[CH3:24][O:25][C:26](=[O:42])[C@@H:27]([NH:41][C:15]([C:12]1[CH:11]=[N:10][C:9]([CH2:8][O:7][C:6]2[CH:18]=[CH:19][CH:20]=[C:4]([O:3][C:2]([F:1])([F:22])[F:21])[CH:5]=2)=[CH:14][N:13]=1)=[O:17])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:31][CH:30]=1

参加物

5

反応物 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 45357110methyl (2S)-2-amino-3-(4-phenylphenyl)propanoate hydrochlorideHCID 692081035-(3-Trifluoromethoxy-phenoxymethyl)-pyrazine-2-carboxylic acid

生成物 1

HCID 692063963-biphenyl-4-yl-2(S)-{[5-(3-trifluoromethoxy-phenoxymethyl)-pyrazine-2-carbonyl]-amino}-propionic acid methyl ester収率 53.2%

実験手順

A solution of 5-(3-trifluoromethoxy-phenoxymethyl)-pyrazine-2-carboxylic acid (0.182 g, 0.579 mmol) was treated with 2(S)-amino-3-biphenyl-4-yl-propionic acid methyl ester hydrochloride (0.162 g, 0.637 mmol), HBTU (0.440 g, 1.158 mmol), and DIEA (0.310 g, 1.737 mmol) by the general procedure A. The crude crude product was purified by flash column chromatography on silica gel to give 0.170 g of 3-biphenyl-4-yl-2(S)-{[5-(3-trifluoromethoxy-phenoxymethyl)-pyrazine-2-carbonyl]-amino}-propionic acid methyl ester. LCMS: 553 (M+2)+

後処理

  1. customThe crude crude product was purified by flash column chromatography on silica gel

出典と根拠

ORDレコード
ord-5917da769e004d4da203112eec4feaaf
出典データセット
uspto-grants-2008_12
特許番号
US07459472B2

関連ノート

読み込み中…