3-Bromo-2-methyl-1-propene → N-(tert-butoxycarbonyl)-N-(2-methylprop-2-enyl)glycine tert-butyl ester

HRID 276270

反応式

HRID 276270 の反応式
[C:1]([O:5][C:6](=[O:16])[CH2:7][NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([CH3:4])([CH3:3])[CH3:2].C[Si](C)(C)[N-][Si](C)(C)C.[Na+].Br[CH2:28][C:29]([CH3:31])=[CH2:30]>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6](=[O:16])[CH2:7][N:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:30][C:29]([CH3:31])=[CH2:28])([CH3:3])([CH3:4])[CH3:2]

参加物

6

反応物 3

HCID 3577853-Bromo-2-methyl-1-propeneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 4097102tert-Butyl ((tert-butoxycarbonyl)amino)acetate

生成物 1

HCID 18316043N-(tert-butoxycarbonyl)-N-(2-methylprop-2-enyl)glycine tert-butyl ester収率 82.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of N-(tert-butoxycarbonyl)glycine tert-butyl ester (3.97 g, 17.2 mmol) in DMF (70 mL) at 0° C. was added sodium hexamethyldisilazide (3.78 g, 20.6 mmol) and the resulting mixture was stirred for 25 min., then allowed to warm to room temp. The resulting solution was treated with 3-bromo-2-methylpropene (2.60 mL, 25.7 mmol), stirred at room temp. for 10 min., and diluted with EtOAc (300 mL). The EtOAc solution was sequentially washed with water (4×500 mL) and a saturated NaCl solution (4×500 mL), dried (MgSO4), and concentrated under reduced pressure to afford N-(tert-butoxycarbonyl)-N-(2-methylprop-2-enyl)glycine tert-butyl ester (4.03 g, 82%): TLC (10% EtOAc/hex) Rf0.51.

後処理

  1. stirringstirred at room temp. for 10 min.
  2. washThe EtOAc solution was sequentially washed with water (4×500 mL)
  3. dry with materiala saturated NaCl solution (4×500 mL), dried (MgSO4)
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-e09cb2a2c9324b9389781078417047af
出典データセット
uspto-grants-2002_03
特許番号
US06353006B1

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