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

HRID 2274545Notes

Reaction equation

HRID 2274545 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].Br[CH2:34][C:35]1[CH:36]=[CH:37][C:38]([NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[N:39][CH:40]=1>C1COCC1.O>[C:19](=[N:18][CH:17]([CH2:34][C:35]1[CH:40]=[N:39][C:38]([NH:41][C:42]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:48])=[CH:37][CH:36]=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-837865d4b17a45b8aea0b62dd339a09e
Source dataset
uspto-grants-2015_09
Patent number
US09126955B2

Reaction notes

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