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

HRID 1780046노트

반응식

HRID 1780046 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-655fddbb85964e588598be4a69caf6d2
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05629419

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