HCID 86589115, compound → HCID 86589114, compound

HRID 2180873Notes

Reaction equation

HRID 2180873 reaction equation
C([O:8][C:9]1[CH:115]=[CH:114][C:12]([CH2:13][C@@H:14]([C:28]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([CH:37]([C:76]3[CH:81]=[CH:80][C:79]([NH:82][C:83](=[O:113])[C@H:84]([CH2:98][C:99]4[CH:104]=[CH:103][C:102]([O:105]CC5C=CC=CC=5)=[CH:101][CH:100]=4)[NH:85][C:86](=[O:97])[CH2:87][C:88]4[C:96]5[C:91](=[CH:92][CH:93]=[CH:94][CH:95]=5)[NH:90][CH:89]=4)=[CH:78][CH:77]=3)[C:38]3[CH:43]=[CH:42][C:41]([NH:44][C:45](=[O:75])[C@H:46]([CH2:60][C:61]4[CH:66]=[CH:65][C:64]([O:67]CC5C=CC=CC=5)=[CH:63][CH:62]=4)[NH:47][C:48](=[O:59])[CH2:49][C:50]4[C:58]5[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=5)[NH:52][CH:51]=4)=[CH:40][CH:39]=3)=[CH:33][CH:32]=2)=[O:29])[NH:15][C:16](=[O:27])[CH2:17][C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.CN(C)C=O.[C].[Pd]>[NH:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18]([CH2:17][C:16]([NH:15][C@H:14]([C:28]([NH:30][C:31]2[CH:32]=[CH:33][C:34]([CH:37]([C:38]3[CH:43]=[CH:42][C:41]([NH:44][C:45](=[O:75])[C@H:46]([CH2:60][C:61]4[CH:62]=[CH:63][C:64]([OH:67])=[CH:65][CH:66]=4)[NH:47][C:48](=[O:59])[CH2:49][C:50]4[C:58]5[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=5)[NH:52][CH:51]=4)=[CH:40][CH:39]=3)[C:76]3[CH:77]=[CH:78][C:79]([NH:82][C:83](=[O:113])[C@H:84]([CH2:98][C:99]4[CH:104]=[CH:103][C:102]([OH:105])=[CH:101][CH:100]=4)[NH:85][C:86](=[O:97])[CH2:87][C:88]4[C:96]5[C:91](=[CH:92][CH:93]=[CH:94][CH:95]=5)[NH:90][CH:89]=4)=[CH:80][CH:81]=3)=[CH:35][CH:36]=2)=[O:29])[CH2:13][C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:115][CH:114]=2)=[O:27])=[CH:19]1

Participants

5

Reactant 1

HCID 86589115HCID 86589115, compound

Product 1

HCID 86589114HCID 86589114, compoundYield 4.2%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

The tris[4-[O-benzyl-N-[2-(1H-indol-3-yl)acetyl]-L-tyrosyl]aminophenyl]methane (70 mg) obtained in Example 92 was dissolved in a mixed solvent of methanol (4 ml) and N,N-dimethylformamide (4 ml), 10% palladium carbon (25 mg) was added, and then the mixture was stirred for 3 days at room temperature under a hydrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. A portion of the residue was purified by preparative high performance liquid chromatography using methanol/trifluoroacetic acid (100/0.1) and water/trifluoroacetic acid (100/0.1) as a mixed eluent, to obtain 2.4 mg of the title compound.

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customA portion of the residue was purified by preparative high performance liquid chromatography

Sources & evidence

ORD record
ord-d3d12455be21418dbd8f4037b527ceee
Source dataset
uspto-grants-2005_05
Patent number
US06887890B2

Reaction notes

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