Sulfuric Acid → 155148-23-5

HRID 1780046Notes

Reaction equation

HRID 1780046 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+]>O>[CH3:2][O:3][C:4](=[O:11])[CH2:5][C@H:6]([Br:17])[C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

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

Product 1

HCID 10656109155148-23-5Yield 101.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-655fddbb85964e588598be4a69caf6d2
Source dataset
uspto-grants-1997_05
Patent number
US05629419

Reaction notes

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