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Hydrochloric Acid → (3R)-8-Cyclopropyl-7-(Naphtalen-1-ylmethyl)-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridine-3,6-dicarboxylic Acid 3-Methyl Ester

HRID 606642
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 606642
[CH3:1][O:2][C:3]([CH:5]1[N:9]2[C:10](=[O:30])[C:11]([CH:28]=[O:29])=[C:12]([CH2:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20][CH:19]=3)[C:13]([CH:14]3[CH2:16][CH2:15]3)=[C:8]2[S:7][CH2:6]1)=[O:4].[O-:31]Cl=O.[Na+].Cl>CS(C)=O.O>[CH3:1][O:2][C:3]([C@H:5]1[N:9]2[C:10](=[O:30])[C:11]([C:28]([OH:31])=[O:29])=[C:12]([CH2:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20][CH:19]=3)[C:13]([CH:14]3[CH2:16][CH2:15]3)=[C:8]2[S:7][CH2:6]1)=[O:4]
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Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 23668197Sodium ChloriteHCID 866117918-Cyclopropyl-6formyl-7-naphthalen-1-ylmethyl-5-oxo-2,3-dihydro-5h-thiazolo[3,2-a]pyridine-3-carboxylic acid methyl ester

Produkt 1

HCID 67047421(3R)-8-Cyclopropyl-7-(Naphtalen-1-ylmethyl)-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridine-3,6-dicarboxylic Acid 3-Methyl EsterAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel
HCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a solution of 2 (100 mg, 0.239 mmol) in dimethylsulfoxide (2.40 mL), NaH2PO4 (66.0 mg, 0.478 mmol), dissolved in water (0.960 mL), was added dropwise at room temperature. The mixture was then kept on ice and NaClO2 (86.0 mg, 0.956 mmol) dissolved in water (0.480 mL), was added dropwise during 30 min. A white precipitate formed. The reaction mixture was stirred in room temperature for 1 h and then poured into a separation funnel containing ice-cooled 1M HCl. The aqueous phase was extracted with CH2Cl2 and the combined organic phases concentrated. The residue was dissolved in H2O:MeCN, 8:2 and freeze dried to yield 5 as a white powder (102 mg, yield: 98%). 1H-NMR (400 Mhz, CDCl3) δ 14.60 (s, 1H, CO2H), 8.21 (d, J=8.32 Hz, 1H, ArH), 7.85 (d, J=7.68 Hz 1H, ArH), 7.67 (d, J=8.14 Hz, 1H, ArH) 7.61-7.45 (m, 2H, ArH) 7.30-7.21 (m, 1H, ArH), 6.69 (d, J=6.72 Hz, 1H, ArH), 5.78 (d, J=8.42 Hz, 1H, ArH), 5.51 (d, J=14.55 Hz, 1H, Nph-CH2) 5.37 (d, J=14.55 Hz, 1H, Nph-CH2) 3.87 (s, 3H, CH3) 3.82-3.72 (m, 1H, SCH2) 3.63-3.54 (m, 1H, SCH2) 1.44-1.32 (m, 1H, CH-cyclopropyl) 0.81-0.64 (m, 2H) 0.56 (sd, 2H, CH2-cyclopropyl) 13C-NMR (100 Mhz, CDCl3) δ 167.59, 165.24, 165.09, 163.75, 154.33, 134.92, 133.84, 132.16, 128.83, 126.78, 126.15, 125.76, 125.51, 123.40, 123.23, 118.68, 112.72, 64.10, 53.84, 33.35, 31.58, 12.10, 8.35, 7.67.

Aufarbeitung

  1. additionwas added dropwise at room temperature
  2. additionwas added dropwise during 30 min
  3. customA white precipitate formed
  4. additionpoured into a separation funnel
  5. additioncontaining ice-
  6. extractionThe aqueous phase was extracted with CH2Cl2
  7. concentrationthe combined organic phases concentrated
  8. dissolutionThe residue was dissolved in H2O
  9. dry with materialMeCN, 8:2 and freeze dried

Quellen und Nachweise

ORD-Eintrag
ord-8176c1964e7f4ff29b65f3e94be72fb6
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07915417B2

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