proline dl-form → HCID 59351677, compound

HRID 1889408Notes

Reaction equation

HRID 1889408 reaction equation
[CH2:1]([C:3]1[S:28][C:6]2[N:7]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:16][CH:15]=3)C(=O)[O:9][C:10](=O)[C:5]=2[CH:4]=1)[CH3:2].[NH:29]1[CH2:36][CH2:35][CH2:34][CH:30]1[C:31]([OH:33])=O>C(O)(=O)C>[CH2:1]([C:3]1[S:28][C:6]2[N:7]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([C:20]4[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:18][CH:19]=3)[C:31](=[O:33])[CH:30]3[CH2:34][CH2:35][CH2:36][N:29]3[C:10](=[O:9])[C:5]=2[CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 614proline dl-formHCID 86642156HCID 86642156, compound

Product 1

HCID 59351677HCID 59351677, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4′-[(6-ethyl-2,4-dioxo-2H-thieno[2,3-d][1,3]oxazine-1(4H)-yl)methyl]biphenyl-2-carbonitrile (1 g), D,L-proline (0.44 g) and acetic acid (50 mL) was stirred at 100° C. for 2 days. The reaction mixture was concentrated under reduced pressure, and purified by silica gel column chromatography to give the title compound as a colorless amorphous solid (0.74 g, 65%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-0adf313bf641426ba31baa12db8f3590
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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