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

HRID 2373854노트

반응식

HRID 2373854 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

실험 절차

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)+

후처리

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

출처 및 근거

ORD 기록
ord-5917da769e004d4da203112eec4feaaf
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07459472B2

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