Sodium hydride → HCID 58355329, compound

HRID 1509576Notes

Reaction equation

HRID 1509576 reaction equation
C(OP([CH2:9][C:10]1[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[N:13]=[N:12][C:11]=1[C:22]([N:24]([CH2:46][CH:47]([CH3:49])[CH3:48])[C@H:25]1[CH2:30][C@@H:29]([C:31]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)=[O:32])[CH2:28][N:27]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:26]1)=[O:23])(OCC)=O)C.[S:50]1[CH:54]=[CH:53][N:52]=[C:51]1[CH:55]=O.[H-].[Na+]>C1COCC1.C(=O)([O-])O.[Na+]>[F:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[N:14]1[C:10](/[CH:9]=[CH:55]/[C:51]2[S:50][CH:54]=[CH:53][N:52]=2)=[C:11]([C:22]([N:24]([CH2:46][CH:47]([CH3:48])[CH3:49])[C@H:25]2[CH2:30][C@@H:29]([C:31]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[O:32])[CH2:28][N:27]([C:39]([O:41][C:42]([CH3:44])([CH3:45])[CH3:43])=[O:40])[CH2:26]2)=[O:23])[N:12]=[N:13]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 27349031,3-Thiazole-2-carbaldehydeHCID 58355171HCID 58355171, compound

Product 1

HCID 58355329HCID 58355329, compoundYield 73.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

tert-Butyl (3S,5R)-3-[({5-[(diethoxyphosphoryl)methyl]-1-(2-fluorophenyl)-1H-1,2,3-triazol-4-yl}carbonyl)(2-methylpropyl)amino]-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylate (470 mg) and 1,3-thiazole-2-carbaldehyde (90 mg) were dissolved in THF (4 ml), sodium hydride (50% in oil, 50 mg) was added under ice-cooling and the mixture was stirred at room temperature for 12 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (10:90-100:0) was concentrated under reduced pressure to give the object product (327 mg).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washa fraction eluted with ethyl acetate-hexane (10:90-100:0)
  7. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-21e4b667e68547f7bef2dd216545a7be
Source dataset
uspto-grants-2015_12
Patent number
US09221836B2

Reaction notes

Loading…