Diethylamine → N-(5,6-dihydrothiazolo[2,3-c][1,2,4]triazol-3-yl)-2-((S)-3-(4-(4-methoxybenzoyl)piperidin-1-yl)-2-oxopyrrolidin-1-yl)acetamide

HRID 1752275Notes

Reaction equation

HRID 1752275 reaction equation
[N:1]1[N:2]=[C:3]([NH:9][C:10](=[O:34])[CH2:11][N:12]2[CH2:16][CH2:15][CH:14]([N:17]3[CH2:22][CH2:21][CH:20]([C:23](=[O:32])[C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=4)[CH2:19][CH2:18]3)[C:13]2=[O:33])[N:4]2[CH2:8][CH2:7][S:6][C:5]=12.ClCCl.C(O)C.C(NCC)C>C(=O)=O>[N:1]1[N:2]=[C:3]([NH:9][C:10](=[O:34])[CH2:11][N:12]2[CH2:16][CH2:15][C@H:14]([N:17]3[CH2:22][CH2:21][CH:20]([C:23](=[O:32])[C:24]4[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=4)[CH2:19][CH2:18]3)[C:13]2=[O:33])[N:4]2[CH2:8][CH2:7][S:6][C:5]=12.[N:1]1[N:2]=[C:3]([NH:9][C:10](=[O:34])[CH2:11][N:12]2[CH2:16][CH2:15][C@@H:14]([N:17]3[CH2:22][CH2:21][CH:20]([C:23](=[O:32])[C:24]4[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=4)[CH2:19][CH2:18]3)[C:13]2=[O:33])[N:4]2[CH2:8][CH2:7][S:6][C:5]=12

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 21584144Dichloromethane ethanolHCID 71212159N-(5,6-dihydrothiazolo[2,3-c][1,2,4]triazol-3-yl)-2-(3-(4-(4-methoxybenzoyl)piperidin-1-yl)-2-oxopyrrolidin-1-yl)acetamide

Product 2

HCID 71212250N-(5,6-dihydrothiazolo[2,3-c][1,2,4]triazol-3-yl)-2-((S)-3-(4-(4-methoxybenzoyl)piperidin-1-yl)-2-oxopyrrolidin-1-yl)acetamideHCID 71212285N-(5,6-dihydrothiazolo[2,3-c][1,2,4]triazol-3-yl)-2-((R)-3-(4-(4-methoxybenzoyl)piperidin-1-yl)-2-oxopyrrolidin-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 280Carbon DioxideSolvent

Procedure

N-(5,6-Dihydrothiazolo[2,3-c][1,2,4]triazol-3-yl)-2-(3-(4-(4-methoxybenzoyl)piperidin-1-yl)-2-oxopyrrolidin-1-yl)acetamide (166 mg, 0.343 mmol) was eluted through a SCF column (70 mL/min flow rate) with 60% CO2 and 40% modifier (composed of 70% dichloromethane/ethanol and 0.2% diethylamine) to yield two enantiomerically enriched peaks N-(5,6-dihydrothiazolo[2,3-c][1,2,4]triazol-3-yl)-2-((S)-3-(4-(4-methoxybenzoyl)piperidin-1-yl)-2-oxopyrrolidin-1-yl)acetamide and N-(5,6-dihydrothiazolo[2,3-c][1,2,4]triazol-3-yl)-2-((R)-3-(4-(4-methoxybenzoyl)piperidin-1-yl)-2-oxopyrrolidin-1-yl)acetamide.

Sources & evidence

ORD record
ord-dda4ea1f8391461ca63ebbea1e0021bb
Source dataset
uspto-grants-2015_10
Patent number
US09163003B2

Reaction notes

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