Tert-butyl 3-methyl-1-oxobutan-2-ylcarbamate → 4-(2-amino-3-methyl-butyl)-6,6-dimethyl-morpholine-3-carboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amide

HRID 552235Notes

Reaction equation

HRID 552235 reaction equation
C(O[C:6]([N:8]1[CH:13]([C:14](=[O:30])[NH:15][C:16]2[CH:17]=[C:18]([Cl:29])[CH:19]=[C:20]3[C:28]=2[NH:27][C:26]2[CH:25]=[N:24][CH:23]=[CH:22][C:21]3=2)[CH2:12][O:11][C:10]([CH3:32])([CH3:31])[CH2:9]1)=O)(C)(C)C.C(OC(=O)[NH:39][CH:40](C=O)[CH:41]([CH3:43])[CH3:42])(C)(C)C>>[Cl:29][C:18]1[CH:19]=[C:20]2[C:28](=[C:16]([NH:15][C:14]([CH:13]3[CH2:12][O:11][C:10]([CH3:32])([CH3:31])[CH2:9][N:8]3[CH2:6][CH:40]([NH2:39])[CH:41]([CH3:43])[CH3:42])=[O:30])[CH:17]=1)[NH:27][C:26]1[CH:25]=[N:24][CH:23]=[CH:22][C:21]2=1

Participants

3

Reactant 2

HCID 545985Tert-butyl 3-methyl-1-oxobutan-2-ylcarbamateHCID 671644975-(6-chloro-9H-beta-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholine-4-carboxylic acid tert-butyl ester

Product 1

HCID 671651234-(2-amino-3-methyl-butyl)-6,6-dimethyl-morpholine-3-carboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amide

Procedure

Method C was followed, using 5-(6-chloro-9H-β-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholine-4-carboxylic acid tert-butyl ester and the appropriate aldehyde, (1-formyl-2-methyl-propyl)-carbamic acid tert-butyl ester. 1H-NMR (DMSO-d6, 300 MHz) δ 9.05 (s, 1); 8.37 (d, 1); 8.21 (d, 1); 8.16 (dd, 1); 7.90 (d, 1); 6.71 (br s, 2); 3.93-3.86 (m, 2); 3.18-3.14 (m, 1); 2.91 (d, 1); 2.70-2.65 (m, 2); 2.21 (dd, 1); 2.15 (d, 1); 1.74-1.66 (m, 1); 1.31 (s, 3); 1.19 (s, 3); 0.85 (d, 3); 0.80 (d, 3). NH4OAc standard conditions. DAD Rf=1.27 min. M+H=444.

Sources & evidence

ORD record
ord-41a5872b7d9b4b59a275acece4a10350
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

Loading…