benzyl 5-[(N-benzyloxycarbonyl-L-alanyl)aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate → 5-(L-alanylaminomethyl)-3,6-dimethoxy-9,9-dimethylxanthene-4-acetic acid

HRID 2395101Notes

Reaction equation

HRID 2395101 reaction equation
C(OC([NH:11][C@H:12]([C:14]([NH:16][CH2:17][C:18]1[C:31]([O:32][CH3:33])=[CH:30][CH:29]=[C:28]2[C:19]=1[O:20][C:21]1[C:22]([CH2:38][C:39]([O:41]CC3C=CC=CC=3)=[O:40])=[C:23]([O:36][CH3:37])[CH:24]=[CH:25][C:26]=1[C:27]2([CH3:35])[CH3:34])=[O:15])[CH3:13])=O)C1C=CC=CC=1>C(O)C(F)(F)F.[Pd]>[NH2:11][C@H:12]([C:14]([NH:16][CH2:17][C:18]1[C:31]([O:32][CH3:33])=[CH:30][CH:29]=[C:28]2[C:19]=1[O:20][C:21]1[C:22]([CH2:38][C:39]([OH:41])=[O:40])=[C:23]([O:36][CH3:37])[CH:24]=[CH:25][C:26]=1[C:27]2([CH3:35])[CH3:34])=[O:15])[CH3:13]

Participants

4

Reactant 1

HCID 67645508benzyl 5-[(N-benzyloxycarbonyl-L-alanyl)aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate

Product 1

HCID 537450725-(L-alanylaminomethyl)-3,6-dimethoxy-9,9-dimethylxanthene-4-acetic acidYield 91.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 64092,2,2-TrifluoroethanolSolvent

Procedure

A solution of 0.3 g of benzyl 5-[(N-benzyloxycarbonyl-L-alanyl)aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate in 85 ml of trifluoroethanol was stirred under hydrogen for 15 minutes in the presence of palladium/charcoal (10%). The catalyst was filtered off and rinsed with trifluoroethanol. The filtrate and wash solution were brought to dryness and the combined residue was chromatographed over silica gel in chloroform/methanol/water, whereby 0.18 g 5-(L-alanylaminomethyl)-3,6-dimethoxy-9,9-dimethylxanthene-4-acetic acid was obtained as a colourless foam, IR 3450-2400, 1679, 1606, 1575, 1493 cm-1.

Workup

  1. filtrationThe catalyst was filtered off
  2. washrinsed with trifluoroethanol
  3. washThe filtrate and wash solution
  4. customthe combined residue was chromatographed over silica gel in chloroform/methanol/water

Sources & evidence

ORD record
ord-af7ed875106543acb14d8f44d85ba193
Source dataset
uspto-grants-1998_09
Patent number
US05811389

Reaction notes

Loading…