Sulfuric Acid → (2S)-2-bromo-4-methoxy-4-oxobutanoic acid

HRID 1780046ノート

反応式

HRID 1780046 の反応式
Cl.[CH3:2][O:3][C:4](=[O:11])[CH2:5][C@H:6](N)[C:7]([OH:9])=[O:8].S(=O)(=O)(O)O.[Br-:17].[K+].N([O-])=O.[Na+]>O>[CH3:2][O:3][C:4](=[O:11])[CH2:5][C@H:6]([Br:17])[C:7]([OH:9])=[O:8]

参加物

6

反応物 4

HCID 1118Sulfuric AcidHCID 253877Potassium BromideHCID 12832742L-Aspartic acid, 4-methyl ester, hydrochloride (1:1)HCID 23668193Sodium Nitrite

生成物 1

HCID 10656109(2S)-2-bromo-4-methoxy-4-oxobutanoic acid収率 101.9%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

To a mixture of (3S)-3-amino-3-carboxypropionic acid methyl ester hydrochloride (155 g), sulfuric acid (433 g), potassium bromide (402 g) and water (1900 ml) is added dropwise a solution of sodium nitrite (69.8 g) in water (150 ml) at a temperature from 10° C. to 12° C. over a period of 45 minutes. After the addition, the mixture is stirred at a temperature from 10° C. to 15° C. for two hours. The reaction solution is extracted with ethyl acetate, and the extract is washed, dried, and concentrated under reduced pressure at a temperature below 35° C. to give (3S)-3-bromo-3-carboxypropionic acid methyl ester (181.5 g) as an oily product.

後処理

  1. additionAfter the addition
  2. extractionThe reaction solution is extracted with ethyl acetate
  3. washthe extract is washed
  4. customdried
  5. concentrationconcentrated under reduced pressure at a temperature below 35° C.

出典と根拠

ORDレコード
ord-655fddbb85964e588598be4a69caf6d2
出典データセット
uspto-grants-1997_05
特許番号
US05629419

反応ノート

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