benzyl 3,6-dimethoxy-9,9-dimethyl-5-[(L-isoleucyl-O-tert-butyl-L-tyrosyl-L-alanyl)aminomethyl]xanthene-4-acetate → 3,6-dimethoxy-9,9-dimethyl-5-[(L-isoleucyl-O-tert-butyl-L-tyrosyl-L-alanyl)aminomethyl]xanthene-4-acetic acid

HRID 2395152Notes

Reaction equation

HRID 2395152 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]([CH3:62])([CH3:61])[C:8]3[C:13]([O:14][C:15]=2[C:16]=1[CH2:17][C:18]([O:20]CC1C=CC=CC=1)=[O:19])=[C:12]([CH2:28][NH:29][C:30](=[O:58])[C@H:31]([CH3:57])[NH:32][C:33](=[O:56])[C@H:34]([CH2:44][C:45]1[CH:50]=[CH:49][C:48]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[CH:47][CH:46]=1)[NH:35][C:36](=[O:43])[C@H:37]([C@H:39]([CH2:41][CH3:42])[CH3:40])[NH2:38])[C:11]([O:59][CH3:60])=[CH:10][CH:9]=3>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]([CH3:62])([CH3:61])[C:8]3[C:13]([O:14][C:15]=2[C:16]=1[CH2:17][C:18]([OH:20])=[O:19])=[C:12]([CH2:28][NH:29][C:30](=[O:58])[C@H:31]([CH3:57])[NH:32][C:33](=[O:56])[C@H:34]([CH2:44][C:45]1[CH:46]=[CH:47][C:48]([O:51][C:52]([CH3:53])([CH3:54])[CH3:55])=[CH:49][CH:50]=1)[NH:35][C:36](=[O:43])[C@H:37]([C@H:39]([CH2:41][CH3:42])[CH3:40])[NH2:38])[C:11]([O:59][CH3:60])=[CH:10][CH:9]=3

Participants

4

Reactant 1

HCID 67644872benzyl 3,6-dimethoxy-9,9-dimethyl-5-[(L-isoleucyl-O-tert-butyl-L-tyrosyl-L-alanyl)aminomethyl]xanthene-4-acetate

Product 1

HCID 676451193,6-dimethoxy-9,9-dimethyl-5-[(L-isoleucyl-O-tert-butyl-L-tyrosyl-L-alanyl)aminomethyl]xanthene-4-acetic acidYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 0.27 g of benzyl 3,6-dimethoxy-9,9-dimethyl-5-[(L-isoleucyl-O-tert-butyl-L-tyrosyl-L-alanyl)aminomethyl]xanthene-4-acetate in 15 ml of methanol was treated with 50 mg of palladium/charcoal (10%) and stirred under hydrogen for 3 hours. After filtering off the catalyst the solvent was removed and the residue was washed with ether. 0.24 g of 3,6-dimethoxy-9,9-dimethyl-5-[(L-isoleucyl-O-tert-butyl-L-tyrosyl-L-alanyl)aminomethyl]xanthene-4-acetic acid of m.p. 146°-149° was obtained; IR 1662, 1606, 1506, 1494 cm-1.

Workup

  1. filtrationAfter filtering off the catalyst the solvent
  2. customwas removed
  3. washthe residue was washed with ether

Sources & evidence

ORD record
ord-62a98dbbd11f446794c54bd7cc6c8e41
Source dataset
uspto-grants-1998_09
Patent number
US05811548

Reaction notes

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