Methyl N-[(benzyloxy)carbonyl]-O-tert-butyl-D-serinate → HCID 7021435, compound

HRID 1908965Notes

Reaction equation

HRID 1908965 reaction equation
C(OC([NH:11][C@H:12]([CH2:17][O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:13]([O:15][CH3:16])=[O:14])=O)C1C=CC=CC=1>CO>[NH2:11][C@H:12]([CH2:17][O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:13]([O:15][CH3:16])=[O:14]

Participants

3

Reactant 1

HCID 7019802Methyl N-[(benzyloxy)carbonyl]-O-tert-butyl-D-serinate

Product 1

HCID 7021435HCID 7021435, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

330.0 L of methanol was added and 66.0 kg of (R)-methyl 2-(benzyloxycarbonylamino)-3-t-butoxypropanoate was added to a hydrogen reactor; and then purged with nitrogen. 4.95 kg of palladium/carbon (10% water mixture) was added and hydrogen was filled to maintain at 5 bar of pressure. It was stirred for 60 minutes, filtered, washed, and then concentrated under reduced pressure. 132.0 L of ethyl acetate and 88 L of water were added to a concentrated residue; stirred for 10 minutes; an organic layer was isolated (in 6 times), dehydrated, and then concentrated under reduced pressure to obtain 27.5 kg of a title compound.

Workup

  1. customand then purged with nitrogen
  2. addition4.95 kg of palladium/carbon (10% water mixture) was added
  3. additionhydrogen was filled
  4. temperatureto maintain at 5 bar of pressure
  5. filtrationfiltered
  6. washwashed
  7. concentrationconcentrated under reduced pressure
  8. addition132.0 L of ethyl acetate and 88 L of water were added to a concentrated residue
  9. stirringstirred for 10 minutes
  10. customan organic layer was isolated (in 6 times)
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dd9843794c894ee085614975663ff591
Source dataset
uspto-grants-2013_12
Patent number
US08598347B2

Reaction notes

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