N-(tert-butoxycarbonyl)-L-aspartic acid → (S)-3-amino-4-(4-((3-fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)picolinamido)methyl)-4-phenylpiperidin-1-yl)-4-oxobutanoic acid

HRID 1800861Notes

Reaction equation

HRID 1800861 reaction equation
[F:1][C:2]1[C:3]([C:22]([NH:24][CH2:25][C:26]2([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[O:23])=[N:4][CH:5]=[CH:6][C:7]=1[S:8][C:9]1[S:13][C:12]([NH:14][C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][N:16]=2)=[N:11][CH:10]=1.C(OC([NH:45][C@@H:46]([CH2:50][C:51]([OH:53])=[O:52])[C:47](O)=[O:48])=O)(C)(C)C>>[NH2:45][C@H:46]([C:47]([N:29]1[CH2:28][CH2:27][C:26]([CH2:25][NH:24][C:22](=[O:23])[C:3]2[C:2]([F:1])=[C:7]([S:8][C:9]3[S:13][C:12]([NH:14][C:15]4[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][N:16]=4)=[N:11][CH:10]=3)[CH:6]=[CH:5][N:4]=2)([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:31][CH2:30]1)=[O:48])[CH2:50][C:51]([OH:53])=[O:52]

Participants

3

Reactant 2

HCID 99718N-(tert-butoxycarbonyl)-L-aspartic acidHCID 250328563-Fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)-N-((4-phenylpiperidin-4-yl)methyl)picolinamide

Product 1

HCID 59321448(S)-3-amino-4-(4-((3-fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)picolinamido)methyl)-4-phenylpiperidin-1-yl)-4-oxobutanoic acid

Procedure

Following the procedure given for example 94, 3-fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)-N-((4-phenylpiperidin-4-yl)methyl)picolinamide (compound example 11) was reacted with (S)-2-(tert-butoxycarbonylamino)succinic acid give the title compound. LC/MS (M+H)+: 650. Ret. time: 1.12 min. (Condition G); analytical HPLC Ret. time: 6.33 min (Condition Q).

Sources & evidence

ORD record
ord-7fea192bec6f4d3b81e6bb05d65103dd
Source dataset
uspto-grants-2013_01
Patent number
US08343999B2

Reaction notes

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