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Water → (1S,3'R,4'S,5'S,6'R)-6'-(azidomethyl)-5-chloro-6-(4-ethylbenzyl)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3',4',5'-triol

HRID 1716963
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1716963
CC1C=CC(S(O[CH2:12][C@H:13]2[O:18][C@@:17]3([C:26]4[C:21](=[CH:22][C:23]([Cl:36])=[C:24]([CH2:27][C:28]5[CH:33]=[CH:32][C:31]([CH2:34][CH3:35])=[CH:30][CH:29]=5)[CH:25]=4)[CH2:20][O:19]3)[C@H:16]([OH:37])[C@@H:15]([OH:38])[C@@H:14]2[OH:39])(=O)=O)=CC=1.[N-:40]=[N+:41]=[N-:42].[Na+].O>CN(C=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[I-]>[N:40]([CH2:12][C@H:13]1[O:18][C@@:17]2([C:26]3[C:21](=[CH:22][C:23]([Cl:36])=[C:24]([CH2:27][C:28]4[CH:33]=[CH:32][C:31]([CH2:34][CH3:35])=[CH:30][CH:29]=4)[CH:25]=3)[CH2:20][O:19]2)[C@H:16]([OH:37])[C@@H:15]([OH:38])[C@@H:14]1[OH:39])=[N+:41]=[N-:42]
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Komponenten

6

Edukt 3

HCID 962WaterHCID 33557Sodium AzideHCID 59013460((1S,3'R,4'S,5'S,6'R)-5-chloro-6-(4-ethylbenzyl)-3',4',5'-trihydroxy-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-6'-yl)methyl 4-methylbenzenesulfonate

Produkt 1

HCID 59013455(1S,3'R,4'S,5'S,6'R)-6'-(azidomethyl)-5-chloro-6-(4-ethylbenzyl)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3',4',5'-triolAusbeute 78,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of ((1S,3′R,4′S,5′S,6′R)-5-chloro-6-(4-ethylbenzyl)-3′,4′,5′-trihydroxy-3′,4′,5′,6′-tetrahydro-3H-spiro[isobenzofuran-1,2′-pyran]-6′-yl)methyl 4-methylbenzenesulfonate (38 mg, 0.066 mmol) in 1 mL of DMF was added sodium azide (22 mg, 0.338 mmol) and a catalytic amount of TBAI. The solution was warmed to 60° C. and kept at the same temperature overnight. 5 mL of water was added and the solution was extracted with ethyl acetate. The combined organic layers were washed with brine prior to drying over sodium sulfate. Concentration under reduced pressure provided the crude product, which was purified by preparative TLC to give 23 mg of title compound. 1H NMR (CD3OD, 400 MHz) δ 7.36 (s, 1H), 7.22 (s, 1H), 7.08 (s, 4H), 5.14 (d, J=12.4 Hz, 1H), 5.09 (d, J=12.4 Hz, 1H), 4.08 (s, 2H), 3.96-3.91 (m, 1H), 3.77-3.70 (m, 2H), 3.52-3.45 (m, 2H), 3.35-3.31 (m, 1H), 2.59 (q, J=7.6 Hz, 2H), 1.20 (t, J=7.6 Hz, 3H); MS ESI (m/z) 446 (M+1)+, calc. 445.

Aufarbeitung

  1. customkept at the same temperature overnight
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialto drying over sodium sulfate
  5. concentrationConcentration under reduced pressure
  6. customprovided the crude product, which
  7. customwas purified by preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-08086a2c1fb94386b2e7e67ec4e8ff17
Quelldatensatz
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07803778B2

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