CO[C:3]([C:5]1([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:10][CH2:9][N:8]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH2:7][CH2:6]1)=[O:4].[OH-].[K+].CCN=C=NCCCN(C)C.[C:42]([C:46]1[CH:52]=[CH:51][C:49]([NH2:50])=[CH:48][CH:47]=1)([CH3:45])([CH3:44])[CH3:43]>CO.CN(C1C=CN=CC=1)C.C(O)(=O)C.O.C1COCC1>[C:25]([O:24][C:22](=[O:23])[NH:21][C:5]1([C:3](=[O:4])[NH:50][C:49]2[CH:51]=[CH:52][C:46]([C:42]([CH3:45])([CH3:44])[CH3:43])=[CH:47][CH:48]=2)[CH2:10][CH2:9][N:8]([S:11]([C:14]2[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=2)(=[O:13])=[O:12])[CH2:7][CH2:6]1)([CH3:28])([CH3:26])[CH3:27]A mixture of 0.493 g (1.195 mmol) 4-tert-Butoxycarbonylamino-1-(toluene-4-sulfonyl)-piperidine-4-carboxylic acid methyl ester and 0.478 mL KOH 5N aq. in a mixture of methanol, THF and water was stirred for 1.5 h at 45° C. The mixture was acidified with acetic acid and evaporated to dryness. The residue was taken up in 2 mL DMF, 28.7 mg (0.154 mmol) EDCI, 18.8 mg (0.309 mmol) DMAP and 23 mg (0.154 mmol) 4-tert.-butyl aniline was added and the mixture was shaken for 24 h at room temperature. The mixture was evaporated to dryness and subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid to yield after evaporation of the product containing fractions 7.9 mg (10%) of the title compound. MS (m/e): 530.2 [(M+H)+].
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