tert-butyl (2S)-2-amino-4-methylpentanoate → tert-butyl N-[2-(2-{[2,4-dihydroxy-5-(propan-2-yl)phenyl]carbonyl}-2,3-dihydro-1H-isoindol-5-yl)ethyl]-L-leucinate

HRID 632574Notes

Reaction equation

HRID 632574 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.[C:40]([O:44][C:45](=[O:52])[C@H:46]([CH2:48][CH:49]([CH3:51])[CH3:50])[NH2:47])([CH3:43])([CH3:42])[CH3:41]>>[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:47][C@H:46]([C:45]([O:44][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:52])[CH2:48][CH:49]([CH3:50])[CH3:51])[CH:34]=2)[CH2:29]1)=[O:27]

Participants

3

Reactant 2

HCID 7022311tert-butyl (2S)-2-amino-4-methylpentanoateHCID 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 54767461tert-butyl N-[2-(2-{[2,4-dihydroxy-5-(propan-2-yl)phenyl]carbonyl}-2,3-dihydro-1H-isoindol-5-yl)ethyl]-L-leucinate

Procedure

Prepared from Intermediate F and L-leucine tert-butyl ester. 1H NMR (300 MHz, d3-MeOD) 7.31-7.12 (4H, m), 6.38 (1H, s), 3.24-3.04 (2H, m), 2.90-2.69 (4H, m), 1.76-1.56 (1H, m), 1.45 (9H, s), 1.23 (6H, d, J=7.0 Hz), 0.93 (6H, dd, J=10.9, 6.6 Hz). LC/MS: purity >98%, m/z 511 [M+H]+

Sources & evidence

ORD record
ord-ef8cd165b2444f7aa5ad595274aa61a5
Source dataset
uspto-grants-2016_04
Patent number
US09321718B2

Reaction notes

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