Sulfuric Acid → 155148-23-5

HRID 1780048Notes

Reaction equation

HRID 1780048 reaction equation
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+].NC(N)=O>O>[CH3:2][O:3][C:4](=[O:11])[CH2:5][C@H:6]([Br:17])[C:7]([OH:9])=[O:8]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 1176UreaHCID 253877Potassium BromideHCID 12832742L-Aspartic acid, 4-methyl ester, hydrochloride (1:1)HCID 23668193Sodium Nitrite

Product 1

HCID 10656109155148-23-5Yield 62.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of (3S)-3-amino-3-carboxypropionic acid methyl ester hydrochloride (206 g), sulfuric acid (552 g), potassium bromide (536 g) and water (2510 ml) is added dropwise a solution of sodium nitrite (93 g) in water (200 ml) at a temperature from 10° C. to 12° C. over a period of 45 minutes. The mixture is stirred at the same temperature for 20 minutes, and thereto is added urea (40 g) in portions. The mixture is extracted with ether, and the extract is washed, dried, and concentrated under reduced pressure to give (3S)-3-bromo-3-carboxypropionic acid methyl ester (148 g) as an oily product.

Workup

  1. extractionThe mixture is extracted with ether
  2. washthe extract is washed
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f74a236c1dbb4e9aba1e690ff30b6bdc
Source dataset
uspto-grants-1997_05
Patent number
US05629419

Reaction notes

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