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

HRID 2373854Notes

Reaction equation

HRID 2373854 reaction equation
[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

Participants

5

Reactant 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

Product 1

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

Procedure

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)+

Workup

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

Sources & evidence

ORD record
ord-5917da769e004d4da203112eec4feaaf
Source dataset
uspto-grants-2008_12
Patent number
US07459472B2

Reaction notes

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