Sodium Bromide → tert-butyl N-((2S)-1-oxobutan-2-yl)carbamate

HRID 1444584

反応式

HRID 1444584 の反応式
[C:1]([C@@H](CC)C(N)O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:14][C:15]1(C)[N:20]([O])C(C)(C)C[CH2:17][CH2:16]1.[Br-].[Na+].C(=O)([O-])[OH:28].[Na+]>ClCCl.O>[C:4]([O:3][C:1]([NH:20][C@@H:15]([CH2:16][CH3:17])[CH:14]=[O:28])=[O:2])([CH3:5])([CH3:6])[CH3:7]

参加物

7

反応物 4

HCID 253881Sodium BromideHCID 516892Sodium BicarbonateHCID 2724126TempoHCID 866023542(S)-Boc-aminobutanol

生成物 1

HCID 10241556tert-butyl N-((2S)-1-oxobutan-2-yl)carbamate収率 77%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 2(S)-Boc-aminobutanol (50 g; 264 mmol) in dichloromethane (500 mL) and water (350 mL) were added at 20° C. TEMPO (0.01 eq), sodium bromide (1 eq) and sodium hydrogencarbonate (3 eq). The reaction mixture was stirred at 0° C. and diluted bleach (1.3 eq, 450 mL) was added over 40 min. The reaction mixture was stirred for 30 min. at 0° C. and then quenched with aq. thiosulfate. After decantation and extractions (dichloromethane), the organic phase was washed with brine, dried and concentrated in vacuo to dryness, giving 2(S)-(tert-butoxycarbonyl)aminobutyraldehyde as a low-melting solid (38.1 g; yield: 77%).

後処理

  1. additiondiluted bleach (1.3 eq, 450 mL)
  2. additionwas added over 40 min
  3. stirringThe reaction mixture was stirred for 30 min. at 0° C.
  4. customquenched with aq. thiosulfate
  5. extractionAfter decantation and extractions (dichloromethane)
  6. washthe organic phase was washed with brine
  7. customdried
  8. concentrationconcentrated in vacuo to dryness

出典と根拠

ORDレコード
ord-8ace0c1e2f3940339049eaef2c9da6ff
出典データセット
uspto-grants-2010_02
特許番号
US07662849B2

関連ノート

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