Trifluoroacetic acid → Benzyl 5-aminomethyl-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate trifluoroacetate

HRID 2395146Notes

Reaction equation

HRID 2395146 reaction equation
C(OC([NH: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]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:32])=[C:15]([O:28][CH3:29])[CH:16]=[CH:17][C:18]=1[C:19]2([CH3:27])[CH3:26])=O)(C)(C)C.[F:41][C:42]([F:47])([F:46])[C:43]([OH:45])=[O:44]>O>[F:41][C:42]([F:47])([F:46])[C:43]([OH:45])=[O:44].[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]([O:33][CH2:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[O:32])=[C:15]([O:28][CH3:29])[CH:16]=[CH:17][C:18]=1[C:19]2([CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67645989Benzyl 5-[(1-tert-butoxyformamido)methyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate

Product 1

HCID 18972493Benzyl 5-aminomethyl-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate trifluoroacetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.9 g (5.29 mmol) of benzyl 5-[(1-tert-butoxyformamido)methyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate were taken up in a mixture of 10 ml of trifluoroacetic acid and 5 ml of water at 0°. After half an hour the solvents were removed, whereupon the residue was treated with 20 ml of ether. The resulting solid was filtered off, washed with ether and dried over magnesium sulphate, whereby 2.25 g of benzyl 5-aminomethyl-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate trifluoroacetate were obtained as a colourless powder of m.p. 169.5°-171°; IR 1716, 1662, 1631, 1604, 1538, 1494 cm-1.

Workup

  1. customAfter half an hour the solvents were removed, whereupon the residue
  2. additionwas treated with 20 ml of ether
  3. filtrationThe resulting solid was filtered off
  4. washwashed with ether
  5. dry with materialdried over magnesium sulphate

Sources & evidence

ORD record
ord-23059100d53741d3846ce79cc44e71aa
Source dataset
uspto-grants-1998_09
Patent number
US05811548

Reaction notes

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