1-Cyclopentyl 1-aminocyclopentanecarboxylate → cyclopentyl 1-{[2-(2-{[2,4-dihydroxy-5-(propan-2-yl)phenyl]carbonyl}-2,3-dihydro-1H-isoindol-5-yl)ethyl]amino}cyclopentanecarboxylate

HRID 632575Notes

Reaction equation

HRID 632575 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[CH2:36][C:35]2[C:30](=[CH:31][CH:32]=[C:33]([CH2:37][CH:38]=O)[CH:34]=2)[CH2:29]1)=[O:27])C1C=CC=CC=1.[CH:40]1([O:45][C:46](=[O:53])[C:47]2([CH2:52][CH2:51][CH2:50][CH2:49]2)[NH2:48])[CH2:44][CH2:43][CH2:42][CH2:41]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[CH2:36][C:35]2[C:30](=[CH:31][CH:32]=[C:33]([CH2:37][CH2:38][NH:48][C:47]3([C:46]([O:45][CH:40]4[CH2:41][CH2:42][CH2:43][CH2:44]4)=[O:53])[CH2:49][CH2:50][CH2:51][CH2:52]3)[CH:34]=2)[CH2:29]1)=[O:27]

Participants

3

Reactant 2

HCID 581390221-Cyclopentyl 1-aminocyclopentanecarboxylateHCID 866864242-(2-{[2,4-bis(benzyloxy)-5-(prop-1-en-2-yl)phenyl]carbonyl}-2,3-dihydro-1H-isoindol-5-yl)acetaldehyde

Product 1

HCID 86686425cyclopentyl 1-{[2-(2-{[2,4-dihydroxy-5-(propan-2-yl)phenyl]carbonyl}-2,3-dihydro-1H-isoindol-5-yl)ethyl]amino}cyclopentanecarboxylate

Procedure

Prepared from Intermediate F and cycloleucine cyclopentyl ester. 1H NMR (300 MHz, d3-MeOD) 6.99-7.20 (4H, m), 6.26 (1H, s) 5.01 (1H, t, J=5.7 Hz), 3.38-3.67 (3H, m), 3.09 (1H, sep, J=6.8 Hz), 2.57-2.75 (4H, m), 1.37-2.15 (16H, m), 1.10 (6H, d, J=6.9 Hz) LC/MS: purity >98%, m/z 521.25 [M+H]+

Sources & evidence

ORD record
ord-fd31245d54894f21a51e94437d110744
Source dataset
uspto-grants-2016_04
Patent number
US09321718B2

Reaction notes

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