Dimethylformamide → HCID 57237383, compound

HRID 373513Notes

Reaction equation

HRID 373513 reaction equation
[CH2:1]([NH:5][C:6]([C@@H:8]1[CH2:27][C@@:16]2([C:20](=[O:21])[N:19]([CH2:22][CH2:23][CH2:24]Cl)[C:18](=[O:26])[NH:17]2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:28])[CH:14]=2)[O:9]1)=[O:7])[CH2:2][CH2:3][CH3:4].[OH:29][CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.C([O-])([O-])=O.[K+].[K+].CN(C)C=O>>[CH2:1]([NH:5][C:6]([C@@H:8]1[CH2:27][C@@:16]2([C:20](=[O:21])[N:19]([CH2:22][CH2:23][CH2:24][N:33]3[CH2:34][CH2:35][CH:30]([OH:29])[CH2:31][CH2:32]3)[C:18](=[O:26])[NH:17]2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:28])[CH:14]=2)[O:9]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79341Piperidin-4-olHCID 57114724HCID 57114724, compound

Product 1

HCID 57237383HCID 57237383, compoundYield 95.4%

Conditions

Temperature
80 °C

Procedure

A mixture of (2S,4S)-N-butyl-1'-(3-chloropropyl)-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carboxamide (Reference Example 4, 17.0 g, 41.4 mmol), 4-hydroxypiperidine (8.36 g, 82.8 mmol), K2CO3 (7.43 g, 53.8 mmol) and N,N-dimethylformamide (68.0 ml, 880 mmol) was stirred for 5 hours at 80° C. After distilling off the solvent, the residue was chromatographed on silica gel, eluted with CH2Cl2 /MeOH (9/1), and evaporated in vacuo to dryness to give amorphous crystals of the desired compound (18.8 g, 95.4%).

Workup

  1. distillationAfter distilling off the solvent
  2. customthe residue was chromatographed on silica gel
  3. washeluted with CH2Cl2 /MeOH (9/1)
  4. customevaporated in vacuo to dryness

Sources & evidence

ORD record
ord-0a68c39a4f9946a3955d57c9c511737c
Source dataset
uspto-grants-1992_11
Patent number
US05164391

Reaction notes

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