2-(1-{[2,4-Bis(benzyloxy)-5-(prop-1-en-2-yl)phenyl]carbonyl}piperidin-4-yl)acetaldehyde → cyclopentyl N-[2-(1-{[2,4-dihydroxy-5-(propan-2-yl)phenyl]carbonyl}piperidin-4-yl)ethyl]-L-alaninate

HRID 632566

Reaction equation

HRID 632566 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([O:15]CC2C=CC=CC=2)[C:12]([C:23]([CH3:25])=[CH2:24])=[CH:11][C:10]=1[C:26]([N:28]1[CH2:33][CH2:32][CH:31]([CH2:34][CH:35]=O)[CH2:30][CH2:29]1)=[O:27])C1C=CC=CC=1.S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH:48]1([O:53][C:54](=[O:58])[C@H:55]([CH3:57])[NH2:56])[CH2:52][CH2:51][CH2:50][CH2:49]1>>[OH:8][C:9]1[CH:14]=[C:13]([OH:15])[C:12]([CH:23]([CH3:24])[CH3:25])=[CH:11][C:10]=1[C:26]([N:28]1[CH2:33][CH2:32][CH:31]([CH2:34][CH2:35][NH:56][C@H:55]([C:54]([O:53][CH:48]2[CH2:52][CH2:51][CH2:50][CH2:49]2)=[O:58])[CH3:57])[CH2:30][CH2:29]1)=[O:27]

Participants

3

Reactant 2

HCID 866864202-(1-{[2,4-Bis(benzyloxy)-5-(prop-1-en-2-yl)phenyl]carbonyl}piperidin-4-yl)acetaldehydeHCID 86686421L-Alanine, cyclopentyl ester, 4-methylbenzenesulfonate (1:1)

Product 1

HCID 54766821cyclopentyl N-[2-(1-{[2,4-dihydroxy-5-(propan-2-yl)phenyl]carbonyl}piperidin-4-yl)ethyl]-L-alaninate

Procedure

Prepared from Intermediate D and L-alanine cyclopentyl ester tosylate. 1H NMR (300 MHz, d3-MeOD) 6.96 (1H, s), 6.34 (1H, s), 5.34 (1H, m), 4.17 (2H, m), 4.07 (1H, m), 3.19 (3H, m), 2.98 (2H, t, J=12 Hz), 1.96 (2H, m), 1.93 (11H, m), 1.56 (3H, d, J=7.2 Hz), 1.29 (2H, m), 1.18 (6H, d, J=6.9 Hz). LC/MS: purity >98%, m/z 447.25 [M+H]+

Sources & evidence

ORD record
ord-d09c7c2f2bfb4a1a818b1bdc696765f4
Source dataset
uspto-grants-2016_04
Patent number
US09321718B2

Linked notes

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