Piperidin-4-ol → (2E)-5-Amino-5-methylhex-2-enoic acid N-((1R)-1-{N-[(1R)-1-(4-fluorobenzyl)-2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]-N-methylcarbamoyl}-2-(2-naphthyl)ethyl)-N-methylamide

HRID 896936Notes

Reaction equation

HRID 896936 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][C:25]([F:28])=[CH:24][CH:23]=1)[C:18]([OH:20])=O)[CH3:16])=[O:14])(C)(C)C.C(O[C:34]([N:36]([C@H:38]([CH2:42][C:43]1[CH:52]=[CH:51][C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:44]=1)C(O)=O)[CH3:37])=[O:35])(C)(C)C.C(OC([NH:60][C:61]([CH3:69])([CH3:68])[CH2:62]/[CH:63]=[CH:64]/C(O)=O)=O)(C)(C)C>>[F:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][C@@H:17]([N:15]([CH3:16])[C:13]([C@H:38]([N:36]([CH3:37])[C:34](=[O:35])/[CH:64]=[CH:63]/[CH2:62][C:61]([NH2:60])([CH3:69])[CH3:68])[CH2:42][C:43]2[CH:52]=[CH:51][C:50]3[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=3)[CH:44]=2)=[O:14])[C:18]([N:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)=[O:20])=[CH:27][CH:26]=1

Participants

5

Reactant 4

HCID 79341Piperidin-4-olHCID 10065151(2R)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-3-naphthalen-2-ylpropanoic acidHCID 10847814(2E)-5-(tert-Butyloxycarbonylamino)-5-methylhex-2-enoic acidHCID 53833009N-Boc-N-methyl-4-fluoro-D-phenylalanine

Product 1

HCID 9960628(2E)-5-Amino-5-methylhex-2-enoic acid N-((1R)-1-{N-[(1R)-1-(4-fluorobenzyl)-2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]-N-methylcarbamoyl}-2-(2-naphthyl)ethyl)-N-methylamide

Procedure

This compound was prepared as in example 1 but using 4-hydroxypiperidine, (2R)-2-(N-tert-butoxycarbonyl-N-methylamino)-3-(4-fluorophenyl)propionic acid and (2R)-2-(N-tert-butoxycarbonyl-N-methylamino)-3-(2-naphthyl)propionic acid and (2E)-5-tert-butoxycarbonylamino-5-methylhex-2-enoic acid as starting materials.

Workup

  1. customThis compound was prepared as in example 1

Sources & evidence

ORD record
ord-430e9fdc26ab4417b288b725ae030872
Source dataset
uspto-grants-2005_07
Patent number
US06919315B1

Reaction notes

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