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

HRID 2395099Notes

Reaction equation

HRID 2395099 reaction equation
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

Participants

6

Reactant 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

Product 1

HCID 207751205-[(9-Fluorenylmethoxyformamido)methyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetic acidYield 60.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3a08afb8fcbe43d8b8f554586a643b47
Source dataset
uspto-grants-1998_09
Patent number
US05811389

Reaction notes

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