5-Oxo-1-phenylpyrrolidine-3-carboxylic acid → HCID 178441301, compound

HRID 76291Notes

Reaction equation

HRID 76291 reaction equation
[C:1]([N:5]1[CH:9]=[C:8]([CH2:10][CH2:11][CH2:12][CH3:13])[C:7](=[NH:14])[S:6]1)([CH3:4])([CH3:3])[CH3:2].[O:15]=[C:16]1[N:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:19][CH:18]([C:27](O)=[O:28])[CH2:17]1>>[CH2:10]([C:8]1=[CH:9][N:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[S:6]/[C:7]/1=[N:14]\[C:27]([CH:18]1[CH2:17][C:16](=[O:15])[N:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:19]1)=[O:28])[CH2:11][CH2:12][CH3:13]

Participants

3

Reactant 2

HCID 27371075-Oxo-1-phenylpyrrolidine-3-carboxylic acidHCID 668672282-tert-Butyl-4-butylisothiazol-5(2H)-imine

Product 1

HCID 178441301HCID 178441301, compound

Procedure

The product from Example 92B and 5-oxo-1-phenylpyrrolidine-3-carboxylic acid (Princeton Bio) were processed using the method described in Example 92C to afford the title compound. 1H NMR (DMSO-d6) δ 0.91 (t, J=7.3 Hz, 3H), 1.26-1.38 (m, 2H), 1.58-1.66 (m, 2H), 1.61 (s, 9H), 2.64-2.69 (m, 2H), 2.85-2.89 (m, 2H), 3.49-3.58 (m, 1H), 4.12 (s, 1H), 4.14 (d, J=1.7 Hz, 1H), 7.08-7.14 (m, 1H), 7.31-7.38 (m, 2H), 7.62-7.68 (m, 2H), 8.48 (s, 1H). (ESI+) m/z 400 (M+H)+.

Sources & evidence

ORD record
ord-b7862bd804624c5c9c0fc4450f351bfb
Source dataset
uspto-grants-2014_09
Patent number
US08835475B2

Reaction notes

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