Sulfuric Acid → Methyl N-[(benzyloxy)carbonyl]-O-tert-butyl-D-serinate

HRID 1908964Notes

Reaction equation

HRID 1908964 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH2:17][OH:18])[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH2:17][O:18][C:2]([CH3:7])([CH3:3])[CH3:1])[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 24436Sodium SulfateHCID 11821096N-Z-D-serine methyl ester

Product 1

HCID 7019802Methyl N-[(benzyloxy)carbonyl]-O-tert-butyl-D-serinateYield 234,010.094%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22.5 °C

Procedure

130 L of methylene chloride was added; 20.5 g of (R)-methyl 2-(benzyloxycarbonylamino)-3-hydroxypropanate to a reactor; then stirred for 30 minutes; and then 0.4 kg of sulfuric acid was added. Isobutylene gas was bubbled for 24 hours while its temperature was maintained at 20-25° C. After completing the reaction, 18 L of saturated sodium hydrogen carbonate aqueous solution was slowly added, stirred for 1 hour, and then an organic layer was isolated. 5 kg of sodium sulfate was added to the organic layer, stirred for 1 hour, filtered, washed, and then the filtrate was concentrated under reduced pressure to obtain 29.3 kg of a title compound.

Workup

  1. customIsobutylene gas was bubbled for 24 hours while its temperature
  2. customthe reaction, 18 L of saturated sodium hydrogen carbonate aqueous solution
  3. additionwas slowly added
  4. stirringstirred for 1 hour
  5. customan organic layer was isolated
  6. stirringstirred for 1 hour
  7. filtrationfiltered
  8. washwashed
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9e4966897f234c70a4482b2105e2a9cb
Source dataset
uspto-grants-2013_12
Patent number
US08598347B2

Reaction notes

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