Lithium Hydroxide → 3-({5-[2-(Pyridin-2-ylamino)-ethylcarbamoyl]-thiophene-2-carbonyl}-amino)-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid methyl ester

HRID 1061722Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1061722
CO[C:3]([C:5]1[S:6][C:7]([C:10](=[O:21])[NH:11][CH2:12][CH2:13][NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:8][CH:9]=1)=[O:4].[Li+].[OH-].N1C=CC=CC=1NCCNC(C1SC(C(O)=O)=CC=1)=O.C(OC(NC[CH2:53][O:54][C:55](=[O:72])[CH:56]([NH:59][S:60]([C:63]1[C:68]([CH3:69])=[CH:67][C:66]([CH3:70])=[CH:65][C:64]=1[CH3:71])(=[O:62])=[O:61])[CH2:57][NH2:58])=O)(C)(C)C.OC1C2N=NNC=2C=CC=1.Cl.C(N=C=N)C>CN(C=O)C>[CH3:53][O:54][C:55](=[O:72])[CH:56]([NH:59][S:60]([C:63]1[C:68]([CH3:69])=[CH:67][C:66]([CH3:70])=[CH:65][C:64]=1[CH3:71])(=[O:62])=[O:61])[CH2:57][NH:58][C:3]([C:5]1[S:6][C:7]([C:10](=[O:21])[NH:11][CH2:12][CH2:13][NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:8][CH:9]=1)=[O:4]

Komponenten

8

Edukt 6

HCID 3939Lithium HydroxideHCID 206776163-Amino-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid 2-tert-butoxycarbonylamino-ethyl esterHCID 21883477Ethylcarbodiimide hydrochlorideHCID 233982735-[2-(Pyridin-2-ylamino)-ethylcarbamoyl]-thiophene-2-carboxylic acid methyl esterHCID 542453455-[2-(Pyridin-2-ylamino)-ethylcarbamoyl]-thiophene-2-carboxylic acidHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 537556273-({5-[2-(Pyridin-2-ylamino)-ethylcarbamoyl]-thiophene-2-carbonyl}-amino)-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid methyl esterAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-[2-(Pyridin-2-ylamino)-ethylcarbamoyl]-thiophene-2-carboxylic acid methyl ester was hydrolyzed with LiOH as described before. To a mixture of 5-[2-(Pyridin-2-ylamino)-ethylcarbamoyl]-thiophene-2-carboxylic acid (38 mg, 0.12 mmol), salt of 3-amino-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid 2-tert-butoxycarbonylamino-ethyl ester (47 mg, 0.14 mmol), hydroxybenzotriazole (21 mg, 0.15 mmol) in DMF (20 mL), was added 1-(3-dimethylamino) propyl)-3-ethylcarbodiimide hydrochloride (29 mg, 0.15 mmol). The reaction was stirred overnight at room temperature. Insolubles were removed by filtration and the solvent was evaporated. Purification of the residue on silica gel (10% MeOH/EtOAc) gave 60 mg (87%) of pure 3-({5-[2-(Pyridin-2-ylamino)-ethylcarbamoyl]-thiophene-2-carbonyl}-amino)-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid methyl ester. 1HNMR (300 MHz, CDCl3) δ: 2.22 (s, 3H), 2.61 (s, 6H), 3.55 (m, 4H), 3.82 (m, 1H), 4.09 (m, 1H), 6.50(d, 1H), 6.69(t, 1H), 6.90(s, 2H), 7.05(t, 1H), 7.40(m, 3H), 8.10 (s, 1H), 8.43(m, 1H).

Aufarbeitung

  1. customInsolubles were removed by filtration
  2. customthe solvent was evaporated
  3. customPurification of the residue on silica gel (10% MeOH/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-cd1649773cca4f5ab7e4db6d498e54d7
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06960594B2

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