Sulfuric Acid → HCID 59516424, compound

HRID 1160474Notes

Reaction equation

HRID 1160474 reaction equation
[C:1](N)(C)(C)C.[OH:6][C:7]1[CH:8]=[C:9]([CH2:13][C@H:14]([O:18][CH:19]([CH3:21])[CH3:20])[C:15]([OH:17])=[O:16])[CH:10]=[CH:11][CH:12]=1.S(=O)(=O)(O)O.C(OC)(C)(C)C>CO>[OH:6][C:7]1[CH:8]=[C:9]([CH2:13][C@H:14]([O:18][CH:19]([CH3:21])[CH3:20])[C:15]([O:17][CH3:1])=[O:16])[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 15413tert-Butyl methyl etherHCID 68423125HCID 68423125, compound

Product 1

HCID 59516424HCID 59516424, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

(2S)-3-(3-Hydroxyphenyl)-2-isopropoxypropionic acid tert-butylamine salt (8.2 kg, 28 mol) was dissolved in methanol (41 L), and then the reaction mixture was cooled to 10° C. Concentrated sulfuric acid (1.9 L, 36 mol) was added to the reaction mixture at 10 to 20° C. over a period of 5 minutes. The reaction mixture was stirred at 60° C. for 3 hours, followed by adding tert-butylmethyl ether (164 L) and a 10% sodium chloride solution (41 L) to separate an organic layer. Then, the organic layer was washed sequentially with the 10% sodium chloride solution (41 L), a 7% sodium bicarbonate aqueous solution (16 L), and water (41 L), followed by vacuum concentration to obtain 6.62 kg of the title compound (yield: 100%). The 1H-NMR data thereof coincided with that of the compound of Example 1-(5).

Workup

  1. customa 10% sodium chloride solution (41 L) to separate an organic layer
  2. washThen, the organic layer was washed sequentially with the 10% sodium chloride solution (41 L)
  3. concentrationa 7% sodium bicarbonate aqueous solution (16 L), and water (41 L), followed by vacuum concentration

Sources & evidence

ORD record
ord-9212b1548ae04602b1b31d609ef9443b
Source dataset
uspto-grants-2010_10
Patent number
US07816405B2

Reaction notes

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