p-Toluenesulfonic acid → HCID 22855833, compound

HRID 54049Notes

Reaction equation

HRID 54049 reaction equation
[C:1]([O:5][C:6](=[O:34])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[CH2:12][C:13](=[O:33])[C@H:14]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[NH:15][C:16](OCC1C=CC=CC=1)=[O:17])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:46][CH:47]([CH3:61])[CH2:48][CH2:49][C:50]([NH:52][C@H:53](C(O)=O)[CH2:54][C:55](=[O:57])[NH2:56])=[O:51]>[Pd]>[C:1]([O:5][C:6](=[O:34])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[CH2:12][C:13](=[O:33])[C@H:14]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[NH:15][C:16](=[O:17])[C@H:53]([CH2:54][C:55](=[O:57])[NH2:56])[NH:52][C:50](=[O:51])[CH2:49][CH2:48][CH:47]([CH3:46])[CH3:61])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 28778444N-(4-methylvaleryl)-L-asparagineHCID 70041054N-[[N-(benzyloxycarbonyl)-L-phenylalanyl]methyl]-L-proline tert.butyl ester

Product 1

HCID 22855833HCID 22855833, compoundYield 27.8%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

0.71 g (1.52 mmol) of N-[[N-(benzyloxycarbonyl)-L-phenylalanyl]methyl]-L-proline tert.butyl ester was hydrogenated in the presence of 0.58 g (3.05 mmol) of toluene-4-sulphonic acid over 5% palladium-on-carbon and the product was coupled with 0.35 g (1.52 mmol) of N-(4-methylvaleryl)-L-asparagine in an analogous manner to that described in Example 1. The crude product was purified by chromatography on silica gel using isopropanol in ethyl acetate (5%-8% gradient) for the elution. There was obtained 0.23 g of N-[[N-[N-(4-methylvaleryl)-L-asparaginyl]-L-phenylalanyl]methyl]-L-proline tert.butyl ester as a solid; MS: m/e 545 [M+H]+.

Workup

  1. customThe crude product was purified by chromatography on silica gel
  2. washfor the elution

Sources & evidence

ORD record
ord-aecba526fb3e4a9b8e7383486447b31f
Source dataset
uspto-grants-1997_04
Patent number
US05620987

Reaction notes

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