(s)-2-Mercaptosuccinic acid → 2-((5S)-2-(2-(1-(tert-butoxycarbonyl)piperidin-4-yl)thiazol-5-yl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetic acid

HRID 1695923

Reaktionsgleichung

[CH3:1][C:2]([CH3:26])([CH3:25])[CH2:3][CH2:4]/[N:5]=[CH:6]\[C:7]1[S:11][C:10]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)=[N:9][CH:8]=1.[SH:27][C@@H:28]([CH2:32][C:33]([OH:35])=[O:34])[C:29](O)=[O:30]>C1(C)C=CC=CC=1>[C:21]([O:20][C:18]([N:15]1[CH2:16][CH2:17][CH:12]([C:10]2[S:11][C:7]([CH:6]3[N:5]([CH2:4][CH2:3][C:2]([CH3:26])([CH3:25])[CH3:1])[C:29](=[O:30])[C@H:28]([CH2:32][C:33]([OH:35])=[O:34])[S:27]3)=[CH:8][N:9]=2)[CH2:13][CH2:14]1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

A mixture of (Z)-tert-butyl 4-(5-((3,3-dimethylbutylimino)methyl)thiazol-2-yl)piperidine-1-carboxylate (290 mg, 0.76 mmol, 1 eq) and (S)-2-mercaptosuccinic acid (138 mg, 0.92 mmol, 1.2 eq) in toluene (20 mL) was heated at 110° C. for 18 hr. The excess solvent was concentrated in vacuo and the solids were collected by filtration. The solids were washed with water, toluene and dried to give 2-((5S)-2-(2-(1-(tert-butoxycarbonyl)piperidin-4-yl)thiazol-5-yl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetic acid (390 mg, 90% yield). (M+1) 512. 1H NMR (CDCl3) δ 7.15 (m, 1H), 5.68 (m, 1H), 4.58-4.11 (m, 3H), 3.62 (m, 1H), 3.39-3.09 (m, 2H), 2.93-2.74 (m, 3H), 2.09 (m, 2H), 1.71-1.64 (m, 2H), 1.47 (s, 9H), 1.44 (m, 1H), 0.85 (s, 9H) ppm.

Aufarbeitung

concentrationThe excess solvent was concentrated in vacuo
filtrationthe solids were collected by filtration
washThe solids were washed with water, toluene
customdried

Quellen und Nachweise

ORD-Eintrag: ord-541d5c5071f141bc96b2c727b1749d81
Quelldatensatz: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08163737B2

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