Diisopropylethylamine → 5-[(9-Fluorenylmethoxyformamido)methyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetic acid

HRID 2395099Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2395099
FC(F)(F)C(O)=O.[NH2:8][CH2:9][C:10]1[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[C:20]2[C:11]=1[O:12][C:13]1[C:14]([CH2:30][C:31]([OH:33])=[O:32])=[C:15]([O:28][CH3:29])[CH:16]=[CH:17][C:18]=1[C:19]2([CH3:27])[CH3:26].[CH:34]1[C:46]2[CH:45]([CH2:47][O:48][C:49](N3C(=O)CCC3=O)=[O:50])[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:38]=2[CH:37]=[CH:36][CH:35]=1.C(N(C(C)C)C(C)C)C>O1CCOCC1.O>[CH:34]1[C:46]2[CH:45]([CH2:47][O:48][C:49]([NH:8][CH2:9][C:10]3[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[C:20]4[C:11]=3[O:12][C:13]3[C:14]([CH2:30][C:31]([OH:33])=[O:32])=[C:15]([O:28][CH3:29])[CH:16]=[CH:17][C:18]=3[C:19]4([CH3:27])[CH3:26])=[O:50])[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:38]=2[CH:37]=[CH:36][CH:35]=1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 108817731-Pyrrolidinecarboxylic acid, 2,5-dioxo-, 9H-fluoren-9-ylmethyl esterHCID 676464795-Aminomethyl-3,6-dimethoxy-9,9-dimethylxanthene-4-acetic acid trifluoroacetate

Produkt 1

HCID 207751205-[(9-Fluorenylmethoxyformamido)methyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetic acidAusbeute 60,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

1.58 g (34.35 mmol) of 5-aminomethyl-3,6-dimethoxy-9,9-dimethylxanthene-4-acetic acid trifluoroacetate were suspended in a mixture of 7 ml of dioxan and 7 ml of water together with 1.13 g (3.35 mmol) of N-(9-fluorenylmethoxycarbonyl)-succinimide, whereupon 0.9 ml (5.03 mmol) of ethyldiisopropylamine was added at 0°. The mixture was stirred at 0° for 2 hours and thereafter at room temperature for 4 hours. The solid obtained was filtered off, washed with water, dried and chromatographed on silica gel with chloroform/methanol. The fractions containing the desired product were combined, washed with dilute potassium hydrogen sulphate solution and thereafter with water, dried over magnesium sulphate and concentrated, whereby 1.17 g of 5-[(9-fluorenylmethoxyformamido)methyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetic acid were obtained as a colourless powder of m.p. 134°-136°; IR 1727, 1703, 1606, 1495 cm-1.

Aufarbeitung

  1. additionwas added at 0°
  2. waitat room temperature for 4 hours
  3. customThe solid obtained
  4. filtrationwas filtered off
  5. washwashed with water
  6. customdried
  7. customchromatographed on silica gel with chloroform/methanol
  8. additionThe fractions containing the desired product
  9. washwashed with dilute potassium hydrogen sulphate solution
  10. dry with materialwith water, dried over magnesium sulphate
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3a08afb8fcbe43d8b8f554586a643b47
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05811389

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