N-(Diphenylmethylene)glycine tert-butyl ester → HCID 58360507, compound

HRID 1023001Notes

Reaction equation

HRID 1023001 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:11]([O:15][C:16](=[O:32])[CH2:17][N:18]=[C:19]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:14])([CH3:13])[CH3:12].[C:33]([O:37][C:38](=[O:48])[NH:39][C:40]1[CH:45]=[CH:44][C:43]([CH2:46]Br)=[CH:42][N:41]=1)([CH3:36])([CH3:35])[CH3:34]>C1COCC1.O>[C:19](=[N:18][CH:17]([CH2:46][C:43]1[CH:42]=[N:41][C:40]([NH:39][C:38]([O:37][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:48])=[CH:45][CH:44]=1)[C:16]([O:15][C:11]([CH3:14])([CH3:12])[CH3:13])=[O:32])([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 688171N-(Diphenylmethylene)glycine tert-butyl esterHCID 2733832Lithium HexamethyldisilazideHCID 23030321tert-Butyl (5-(bromomethyl)pyridin-2-yl)carbamate

Product 1

HCID 58360507HCID 58360507, compoundYield 103.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

84.64 ml (84.64 mmol) of a 1M solution of lithium bis(trimethylsilyl)amide in THF were added dropwise to a solution of 25.00 g (84.64 mmol) of N-(diphenylmethylene)glycine tert-butyl ester in 185 ml of THF under argon at 0° C. After stirring at this temperature for 15 min, 24.31 g (84.64 mmol) of tert-butyl(5-bromomethylpyridin-2-yl)carbamate were added as solid, and stirring was continued for 1 h. The reaction mixture was cautiously diluted with water and extracted with ethyl acetate. The organic phase was dried over sodium sulfate, filtered and concentrated. 44.08 g of the crude product were obtained and were reacted further without further purification.

Workup

  1. stirringstirring
  2. waitwas continued for 1 h
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-94ded5b94c384efea6e8674a0287dd1b
Source dataset
uspto-grants-2014_05
Patent number
US08722655B2

Reaction notes

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