Hydrochloric Acid → HCID 59516434, compound

HRID 1160470Notes

Reaction equation

HRID 1160470 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C@H:9]([OH:14])[C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:22](Cl)(=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24].Cl>C(OC)(C)(C)C>[C:22]([O:1][C:2]1[CH:3]=[C:4]([CH2:8][C@H:9]([OH:14])[C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][CH:7]=1)(=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 59516428HCID 59516428, compound

Product 1

HCID 59516434HCID 59516434, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
10 °C

Procedure

Methyl (2S)-3-(3-hydroxyphenyl)-2-hydroxypropionate (8.93 kg, 45.1 mol) was dissolved in tert-butylmethyl ether (133 L), and triethylamine (12.7 L, 91 mol) was added to the reaction mixture at room temperature, followed by cooling. Pivaloyl chloride (5.89 L, 48 mol) was added dropwise to the reaction mixture at an internal temperature of 2° C. After the end of the dropwise addition, the reaction mixture was stirred at 10° C. for 17 hours. To the reaction mixture was added 43 L of a 1N hydrochloric acid aqueous solution before stirring, followed by allowing to stand and then separating the mixture. The organic layer was washed twice each with a 0.25N sodium hydroxide aqueous solution (45 L) and water (45 L), and further washed with 42 L of a 5% sodium chloride solution, and then the organic layer was subjected to vacuum concentration at 50° C. After that, 1,2-dimethoxyethane (45 L) was added to the residue and then again subjected to vacuum concentration to obtain 11.0 kg of the title compound (yield: 86%).

Workup

  1. temperatureby cooling
  2. additionAfter the end of the dropwise addition
  3. stirringbefore stirring
  4. customseparating the mixture
  5. washThe organic layer was washed twice each with a 0.25N sodium hydroxide aqueous solution (45 L) and water (45 L)
  6. washfurther washed with 42 L of a 5% sodium chloride solution
  7. concentrationthe organic layer was subjected to vacuum concentration at 50° C
  8. additionAfter that, 1,2-dimethoxyethane (45 L) was added to the residue
  9. concentrationagain subjected to vacuum concentration

Sources & evidence

ORD record
ord-04cc9e58ac1d47e8939ffa6d8b6204f7
Source dataset
uspto-grants-2010_10
Patent number
US07816405B2

Reaction notes

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