Sodium hydride → N-Boc-O-(2-nitrophenyl)-D-serine

HRID 53124ノート

反応式

HRID 53124 の反応式
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C@@H:11]([C:14]([OH:16])=[O:15])[CH2:12][OH:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].F[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25]>CN(C=O)C>[N+:24]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[O:13][CH2:12][C@H:11]([C:14]([OH:16])=[O:15])[NH:10][C:8]([O:7][C:3]([CH3:6])([CH3:4])[CH3:5])=[O:9])([O-:26])=[O:25]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzeneHCID 637603(R)-2-tert-butoxycarbonylamino-3-hydroxy propionic acid

生成物 1

HCID 54196434N-Boc-O-(2-nitrophenyl)-D-serine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of 1.84 g (0.0768M) of sodium hydride (NaH) in 50 mL of DMF at 0° C. under a nitrogen atmosphere was added dropwise a slurry of 7.39 g (0.0360M) of N-t-butoxycarbonyl-D-serine. After addition was complete, the reaction was warmed to room temperature and stirred for 45 minutes. The reaction was cooled to -5° C. and 4.04 mL (0.0384M) of 2-fluoronitrobenzene was added dropwise. The reaction was then warmed to room temperature and stirred for 1 hour. The reaction was quenched with an equal volume of water and extracted with ethyl acetate. The ethyl acetate extracts were reextracted with water (pH=9). The water layer was then adjusted to pH=7 and extracted with ethyl acetate. The water layer was then adjusted to pH=2 and extracted with ethyl acetate. The pH=2 ethyl acetate extracts were combined, dried, and evaporated to yield 8.98 g of product as an oil.

後処理

  1. additionAfter addition
  2. temperatureThe reaction was cooled to -5° C.
  3. temperatureThe reaction was then warmed to room temperature
  4. stirringstirred for 1 hour
  5. customThe reaction was quenched with an equal volume of water
  6. extractionextracted with ethyl acetate
  7. extractionextracted with ethyl acetate
  8. extractionextracted with ethyl acetate
  9. customdried
  10. customevaporated

出典と根拠

ORDレコード
ord-b17446105a5d414897632b90abebcc61
出典データセット
uspto-grants-1997_04
特許番号
US05618808

反応ノート

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