(R)-2-((tert-Butoxycarbonyl)amino)-2-methylbutanoic acid → tert-butyl (2R)-2-methyl-1-[(2R)-3-(1-methyl-1H-indol-3-yl)-1-oxo-1-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-ylamino]propan-2-ylamino]-1-oxobutan-2-ylcarbamate

HRID 2070154Notes

Reaction equation

HRID 2070154 reaction equation
[NH2:1][C@H:2]([CH2:29][C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:32]([CH3:39])[CH:31]=1)[C:3]([NH:5][CH:6]1[CH2:15][C:14]2[C:9](=[C:10]([N:16]3[CH2:20][CH2:19][CH2:18][C:17]3=[O:21])[CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:22][C:23]2[CH:27]=[CH:26][S:25][CH:24]=2)[C:7]1=[O:28])=[O:4].[C:40]([O:44][C:45]([NH:47][C@:48]([CH3:54])([CH2:52][CH3:53])[C:49](O)=[O:50])=[O:46])([CH3:43])([CH3:42])[CH3:41]>>[CH3:54][C@@:48]([NH:47][C:45](=[O:46])[O:44][C:40]([CH3:43])([CH3:42])[CH3:41])([CH2:52][CH3:53])[C:49]([NH:1][C@H:2]([CH2:29][C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:32]([CH3:39])[CH:31]=1)[C:3](=[O:4])[NH:5][CH:6]1[CH2:15][C:14]2[C:9](=[C:10]([N:16]3[CH2:20][CH2:19][CH2:18][C:17]3=[O:21])[CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:22][C:23]2[CH:27]=[CH:26][S:25][CH:24]=2)[C:7]1=[O:28])=[O:50]

Participants

3

Reactant 2

HCID 14284791(R)-2-((tert-Butoxycarbonyl)amino)-2-methylbutanoic acidHCID 44193684(2R)-2-amino-3-(1-methyl-1H-indol-3-yl)-N-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-yl]propanamide

Product 1

HCID 59620374tert-butyl (2R)-2-methyl-1-[(2R)-3-(1-methyl-1H-indol-3-yl)-1-oxo-1-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-ylamino]propan-2-ylamino]-1-oxobutan-2-ylcarbamateYield 89.4%

Procedure

The procedure of Example 14(a) was repeated, except that (2R)-2-amino-3-(1-methyl-1H-indol-3-yl)-N-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-yl]propanamide obtained in Example 8(b) (5.4 g) and (R)-2-(tert-butoxycarbonylamino)-2-methylbutanoic acid (2.4 g) were used, whereby the title compound (6.6 g) was yielded.

Sources & evidence

ORD record
ord-4754de5e67a044ab8cc641201d5c3b47
Source dataset
uspto-grants-2012_10
Patent number
US08299255B2

Reaction notes

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