HCID 67646864, compound → HCID 67647002, compound

HRID 2395109Notes

Reaction equation

HRID 2395109 reaction equation
C(OC([NH:11][C@H:12]([C:14]([NH:16][C@H:17]([C:25]([NH:27][C@H:28]([C:32]([NH:34][CH2:35][C:36]([NH:38][CH2:39][C:40]1[C:53]([O:54][CH3:55])=[CH:52][CH:51]=[C:50]2[C:41]=1[O:42][C:43]1[C:44]([CH2:60][C:61]([O:63][CH3:64])=[O:62])=[C:45]([O:58][CH3:59])[CH:46]=[CH:47][C:48]=1[C:49]2([CH3:57])[CH3:56])=[O:37])=[O:33])[CH:29]([CH3:31])[CH3:30])=[O:26])[C@@H:18]([CH3:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:15])[CH3:13])=O)C1C=CC=CC=1>O1CCOCC1.[Pd]>[NH2:11][C@H:12]([C:14]([NH:16][C@H:17]([C:25]([NH:27][C@H:28]([C:32]([NH:34][CH2:35][C:36]([NH:38][CH2:39][C:40]1[C:53]([O:54][CH3:55])=[CH:52][CH:51]=[C:50]2[C:41]=1[O:42][C:43]1[C:44]([CH2:60][C:61]([O:63][CH3:64])=[O:62])=[C:45]([O:58][CH3:59])[CH:46]=[CH:47][C:48]=1[C:49]2([CH3:57])[CH3:56])=[O:37])=[O:33])[CH:29]([CH3:31])[CH3:30])=[O:26])[C@@H:18]([CH3:24])[O:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:15])[CH3:13]

Participants

4

Reactant 1

HCID 67646864HCID 67646864, compound

Product 1

HCID 67647002HCID 67647002, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 70 mg of methyl 5-[(N-benzyloxycarbonyl-L-alanyl-O-tert-butyl-L-threonyl-L-valyl-glycyl)aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate in 20 ml of dioxan was treated with 47 mg of palladium/charcoal (10%) and stirred under hydrogen for 19 hours. After filtering off the catalyst the filtrate was concentrated, whereby 59 mg of colourless methyl 5-[(L-alanyl-O-tert-butyl-L-threonyl-L-valyl-glycyl)aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate was obtained; IR 3300, 2970, 1741, 1680, 1658, 1631, 1523, 1494 cm-1.

Workup

  1. filtrationAfter filtering off the catalyst the filtrate
  2. concentrationwas concentrated

Sources & evidence

ORD record
ord-f69f9f38b7074761a11dd0bcacc386be
Source dataset
uspto-grants-1998_09
Patent number
US05811389

Reaction notes

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