Ethanol → (4S)-4-[(tert-Butoxycarbonyl)amino]-5-ethoxy-5-oxopentanoic acid

HRID 1468306Notes

Reaction equation

HRID 1468306 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@H:9]([C:22]([OH:24])=[O:23])[CH2:10][CH2:11][C:12]([O:14]CC1C=CC=CC=1)=[O:13])=[O:7])([CH3:4])[CH3:3].O.ON1[C:31]2C=CC=C[C:30]=2N=N1.C(O)C>C(Cl)Cl>[NH:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C@H:9]([C:22]([O:24][CH2:30][CH3:31])=[O:23])[CH2:10][CH2:11][C:12](=[O:13])[OH:14]

Participants

5

Reactant 3

HCID 702EthanolHCID 83589L-Glutamic acid, N-((1,1-dimethylethoxy)carbonyl)-, 5-(phenylmethyl) esterHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 13819298(4S)-4-[(tert-Butoxycarbonyl)amino]-5-ethoxy-5-oxopentanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Boc-Glu (OBzl)-OH, 1.01 g (3.0 mmol), 620 mg (3.1 mmol) of N,N-dicyclohexylcarbodiimide (DCC) and 475 mg (3.1 mmol) of 1-hydroxybenzotriazole monohydrate (HOBt.H2O) were suspended in 12 ml of methylene chloride. The suspension was cooled to 0° C. and 175 μl of ethyl alcohol was added thereto. After reverting to room temperature, stirring was continued overnight. The mixture was extracted with ethyl acetate/water. After the organic layer was washed with aqueous saturated sodium chloride solution (brine), sodium sulfate was added thereto and dried. The organic layer was concentrated under reduced pressure. The resulting residue was dissolved in 12 ml of methanol, and 100 mg of 10% Pd/C was added to the solution. The mixture was stirred in a hydrogen atmosphere overnight and purified in accordance with the purification step A to give the crude product of the title compound.

Workup

  1. customAfter reverting to room temperature
  2. extractionThe mixture was extracted with ethyl acetate/water
  3. washAfter the organic layer was washed with aqueous saturated sodium chloride solution (brine), sodium sulfate
  4. additionwas added
  5. customdried
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. dissolutionThe resulting residue was dissolved in 12 ml of methanol
  8. addition100 mg of 10% Pd/C was added to the solution
  9. stirringThe mixture was stirred in a hydrogen atmosphere overnight
  10. custompurified in accordance with the purification step A

Sources & evidence

ORD record
ord-61cf387c2f334d00bb079c8a5103acd4
Source dataset
uspto-grants-2015_04
Patent number
US09000208B2

Reaction notes

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