1-Hydroxybenzotriazole → HCID 131723034, Verbindung

HRID 393073Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 393073
[Cl:1][C:2]1[CH:10]=[C:9]([C:11](=[O:21])[CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.[CH3:23][O:24][C:25](=[O:37])[C@H:26]([CH2:28][NH:29][C:30]([C:32]1[S:33][CH:34]=[CH:35][CH:36]=1)=[O:31])[NH2:27].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]([OH:21])[CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=2)[CH:8]=[CH:7][C:3]=1[C:4]([NH:27][C@H:26]([C:25]([O:24][CH3:23])=[O:37])[CH2:28][NH:29][C:30]([C:32]1[S:33][CH:34]=[CH:35][CH:36]=1)=[O:31])=[O:6]

Komponenten

7

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 226613772-Chloro-4-[1-oxo-3-(3-hydroxyphenyl)propyl]benzoic acidHCID 688207093-(thiophene-2-carbonyl)amino-L-alanine methyl ester hydrochloride

Produkt 1

HCID 131723034HCID 131723034, VerbindungAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2-chloro-4-[1-oxo-3-(3-hydroxyphenyl)propyl]benzoic acid (Example 41; 75.8 mg, 0.25 mmol), 3-(thiophene-2-carbonyl)amino-L-alanine, methyl ester hydrochloride (Example 301; 73 mg, 0.28 mmol), HBTU (113 mg, 0.30 mmol), HOBT (41 mg, 0.27 mmol) and diisopropylethylamine (0.22 mL, 1.26 mmol) in N,N-dimethylformamide (6 mL) was stirred overnight at room temperature. The solvent was evaporated. Ethyl acetate (30 mL) was added and the solution was washed with sodium hydrogen carbonate solution and 0.5 M HCl. Each of the aqueous layers was extracted with ethyl acetate (10 mL) and the combined organic layers were dried (Na2SO4), filtered, evaporated, and chromatographed (10-100% ethyl acetate/hexanes) to give N-[2-chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)propyl]benzoyl]-3-(thiophene-2-carbonyl)amino-L-alanine, methyl ester (125 mg, 98%).

Aufarbeitung

  1. customThe solvent was evaporated
  2. additionEthyl acetate (30 mL) was added
  3. washthe solution was washed with sodium hydrogen carbonate solution and 0.5 M HCl
  4. extractionEach of the aqueous layers was extracted with ethyl acetate (10 mL)
  5. dry with materialthe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customchromatographed (10-100% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-9cb74b4a4e37481189c374d5401251c9
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06803384B2

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