Piperidin-4-ol → (2E)-4-(1-Aminocyclobutyl)but-2-enoic acid N-((1R)-1-{N-[(1R)-1-benzyl-2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]-N-methylcarbamoyl}-2-(2-naphthyl)ethyl)-N-methylamide

HRID 2104341Notes

Reaction equation

HRID 2104341 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(OC([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)(C)(C)C.C(O[C:33]([N:35]([C@H:37]([CH2:41][C:42]1[CH:51]=[CH:50][C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:43]=1)[C:38]([OH:40])=O)[CH3:36])=[O:34])(C)(C)C.C(OC([NH:59][C:60]1([CH2:64]/[CH:65]=[CH:66]/C(O)=O)[CH2:63][CH2:62][CH2:61]1)=O)(C)(C)C>>[CH2:21]([C@@H:17]([N:15]([CH3:16])[C:38]([C@H:37]([N:35]([CH3:36])[C:33](=[O:34])/[CH:66]=[CH:65]/[CH2:64][C:60]1([NH2:59])[CH2:63][CH2:62][CH2:61]1)[CH2:41][C:42]1[CH:51]=[CH:50][C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:43]=1)=[O:40])[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 10065151(2R)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-3-naphthalen-2-ylpropanoic acidHCID 10729698(2E)-4-(1-{[(tert-butoxy)carbonyl]amino}cyclobutyl)but-2-enoic acid

Product 1

HCID 9895138(2E)-4-(1-Aminocyclobutyl)but-2-enoic acid N-((1R)-1-{N-[(1R)-1-benzyl-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-phenylpropionic acid and (2R)-2-(N-tert-butoxycarbonyl-N-methylamino)-3-(2-naphthyl)propionic acid and (2E)-4-(1-(tert-butoxycarbonylamino)cyclobutyl)but-2-enoic acid.

Workup

  1. customThis compound was prepared as in example 1

Sources & evidence

ORD record
ord-c8a09a88a5c4404aa77f19970204fe7b
Source dataset
uspto-grants-2009_08
Patent number
US07576062B2

Reaction notes

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