Ethanol → HCID 57650547, compound

HRID 2063482Notes

Reaction equation

[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][C:7](=[CH:22][N:23](C)[CH3:24])[C:8]([C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=O)=[CH:4][CH:3]=1.[O-]CC.[Na+].C(O)C.C(O)(=O)C.C(N)=[NH:40]>C(O)CCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[C:8]([C@H:10]3[CH2:14][CH2:13][CH2:12][N:11]3[C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])=[N:40][CH:24]=[N:23][CH:22]=2)=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of (R)-tert-butyl 2-(2-(4-chlorobenzyl)-3-(dimethylamino)acryloyl)pyrrolidine-1-carboxylate (1.5 mmol) in n-butanol (10 mL) was added sodium ethoxide in ethanol (5.6 mL, 21 wt. %, 15 mmol) and formamidine acetate (1.56 g, 15 mmol). The reaction mixture was heated at 90° C. for 12 h. After removal of the solvents in vacuo, the residue was dissolved in ethyl acetate. The organic layer was washed with brine three times, dried over sodium sulfate and the solvent was removed in vacuo. Purification by silica gel column chromatography (ethyl acetate/hexane gradient, 10-100% EtOAc) afforded the desired product (320 mg, combined yield for step B and step C was 57%). MS: calculated: 373.16 found (MH+): 374.4.

Workup

customAfter removal of the solvents in vacuo
dissolutionthe residue was dissolved in ethyl acetate
washThe organic layer was washed with brine three times
dry with materialdried over sodium sulfate
customthe solvent was removed in vacuo
customPurification by silica gel column chromatography (ethyl acetate/hexane gradient, 10-100% EtOAc)

Sources & evidence

ORD record: ord-d53159f349d443fa865a72293e934f99
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288371B2

Reaction notes

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