alpha,alpha-Dimethylglycine cyclopentyl ester → cyclopentyl N-[2-(1-{[2,4-dihydroxy-5-(propan-2-yl)phenyl]carbonyl}piperidin-4-yl)ethyl]-2-methylalaninate

HRID 632571

Reaction equation

HRID 632571 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.[CH:37]1([O:42][C:43](=[O:48])[C:44]([CH3:47])([CH3:46])[NH2:45])[CH2:41][CH2:40][CH2:39][CH2:38]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:45][C:44]([CH3:46])([C:43]([O:42][CH:37]2[CH2:38][CH2:39][CH2:40][CH2:41]2)=[O:48])[CH3:47])[CH2:30][CH2:29]1)=[O:27]

Participants

3

Reactant 2

HCID 59622352alpha,alpha-Dimethylglycine cyclopentyl esterHCID 866864202-(1-{[2,4-Bis(benzyloxy)-5-(prop-1-en-2-yl)phenyl]carbonyl}piperidin-4-yl)acetaldehyde

Product 1

HCID 54767291cyclopentyl N-[2-(1-{[2,4-dihydroxy-5-(propan-2-yl)phenyl]carbonyl}piperidin-4-yl)ethyl]-2-methylalaninate

Procedure

Prepared from Intermediate D and α,α-dimethylglycine cyclopentyl ester. 1H NMR (300 MHz, d3-MeOD) 6.96 (1H, s), 6.34 (1H, s), 5.26-5.39 (1H, m), 4.29 (2H, br. s.), 3.28 (1H, br. s.), 3.18 (1H, dt, J=13.6, 6.8 Hz), 3.03-3.12 (2H, m), 2.98 (2H, t, J=12.4 Hz), 1.64-2.01 (11H, m), 1.59 (6H, s), 1.24-1.38 (3H, m), 1.19 (6H, d, J=7.0 Hz) LC/MS: purity 97%, m/z 461 [M+H]+

Sources & evidence

ORD record
ord-3c54ef227f12412894e3950eb3be9a22
Source dataset
uspto-grants-2016_04
Patent number
US09321718B2

Linked notes

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