Piperidin-4-ol → (2E)-5-Methyl-5-(methylamino)hex-2-enoic acid N-((1R)-1-{N-[(1R)-1-benzyl-2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]-N-methylcarbamoyl}-2-(biphenyl-4-yl)ethyl)-N-methylamide

HRID 2104345Notes

Reaction equation

HRID 2104345 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(O[C:13]([N:15]([C@H:17]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:18]([OH:20])=O)[CH3:16])=[O:14])(C)(C)C.C(O[C:33]([N:35]([C@H:37]([CH2:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[CH:44][CH:43]=1)C(O)=O)C)=O)(C)(C)C.C(OC([N:61]([C:63]([CH3:71])([CH3:70])[CH2:64]/[CH:65]=[CH:66]/[C:67]([OH:69])=O)[CH3:62])=O)(C)(C)C>>[CH2:21]([C@@H:17]([N:15]([CH3:16])[C:13]([C@H:37]([N:35]([CH3:33])[C:67](=[O:69])/[CH:66]=[CH:65]/[CH2:64][C:63]([CH3:70])([NH:61][CH3:62])[CH3:71])[CH2:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)=[CH:44][CH:43]=1)=[O:14])[C:18]([N:5]1[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]1)=[O:20])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 4

HCID 79341Piperidin-4-olHCID 7015127N-Boc-N-methyl-D-phenylalanineHCID 10848750(2E)-5-(N-(tert-butoxycarbonyl)-N-methylamino)-5-methylhex-2-enoic acidHCID 20694694N-Boc-N-methyl-3-(biphenyl-4-yl)-D-alanine

Product 1

HCID 60017965(2E)-5-Methyl-5-(methylamino)hex-2-enoic acid N-((1R)-1-{N-[(1R)-1-benzyl-2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]-N-methylcarbamoyl}-2-(biphenyl-4-yl)ethyl)-N-methylamide

Procedure

The title compound was prepared as in example 1 but using 4-hydroxypiperidine, (2R)-2-(N-tert-butoxycarbonyl-N-methylamino)-3-phenylpropionic acid and (2R)-2-(N-tert-butoxycarbonyl-N-methylamino)-3-(biphenyl-4-yl)propionic acid and (2E)-5-(N-(tert Butoxycarbonyl)-N-methylamino)-5-methylhex-2-enoic acid as starting materials

Sources & evidence

ORD record
ord-7e31fba4797849f99a7685f2744fa78e
Source dataset
uspto-grants-2009_08
Patent number
US07576062B2

Reaction notes

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