p-Toluenesulfonic acid → HCID 70041042, compound

HRID 54050

Reaction equation

HRID 54050 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(OCC1C=CC=CC=1)=O)([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:46]([O:53][C:54]([NH:56][C@H:57]([C:59]([OH:61])=O)[CH3:58])=[O:55])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.C1(N=C=NC2CCCCC2)CCCCC1.OC1C2N=NNC=2C=CC=1.C(N1CCOCC1)C>C(OCC)(=O)C.C(O)(C)C.[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:59](=[O:61])[C@H:57]([CH3:58])[NH:56][C:54]([O:53][CH2:46][C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1)=[O:55])([CH3:4])([CH3:2])[CH3:3]

Participants

10

Reactant 6

HCID 6101p-Toluenesulfonic acidHCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 736104N-carbobenzyloxyalanineHCID 70041054HCID 70041054, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 70041042HCID 70041042, compoundYield 36.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.3 g (2.79 mmol) of N-[[N-(benzyloxycarbonyl)-L-phenylalanyl]methyl]-L-proline tert.butyl ester was hydrogenated in a mixture of 10 ml of ethyl acetate and 10 ml of isopropyl alcohol in the presence of 0.39 g of 5% palladium-on-carbon and 1.06 g (5.58 mmol) of toluene-4-sulphonic acid and the product was coupled with 0.62 g (2.78 mmol) of N-(benzyloxycarbonyl)-L-alanine in the presence of 0.572 g (2.78 mmol) of dicyclohexylcarbodiimide, 0.375 g (2.78 mmol) of hydroxybenzotriazole and 0.64 g (5.57 mmol) of N-ethylmorpholine in a manner analogous to that described in Example 1. After working-up and chromatography on silica gel using 3% isopropanol in dichloromethane for the elution there was obtained 0.55 g of N-[[N-[N-(benzyloxycarbonyl)-L-alanyl]-L-phenylalanyl]methyl]-L-proline tert.butyl ester as a solid: MS: m/e 538 [M+H]+.

Workup

  1. washchromatography on silica gel using 3% isopropanol in dichloromethane for the elution there

Sources & evidence

ORD record
ord-bf8811fec9bd460b876244d610a99ed6
Source dataset
uspto-grants-1997_04
Patent number
US05620987

Linked notes

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