Ammonia → HCID 2734757, compound

HRID 1746832Notes

Reaction equation

HRID 1746832 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@H:9]([C:22]([OH:24])=O)[CH2:10][CH2:11][C:12]([O:14]CC1C=CC=CC=1)=[O:13])=[O:7])([CH3:4])[CH3:3].ClC(OCC)=O.C([N:33](CC)CC)C.N.[H][H]>O1CCCC1.[Pd].CO>[C:2]([O:5][C:6]([NH:8][C@H:9]([C:22](=[O:24])[NH2:33])[CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:1]

Participants

9

Reactant 5

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 83589L-Glutamic acid, N-((1,1-dimethylethoxy)carbonyl)-, 5-(phenylmethyl) esterHCID 178418361HCID 178418361, compound

Product 1

HCID 2734757HCID 2734757, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1010 mg (3.0 mmol) of Boc-Glu (OBzl)-OH, 316 μl (3.3 mmol) of ethyl chloroformate and 460 μl (3.3 mmol) of triethylamine were suspended in 12.0 ml of tetrahydrofuran, to which 2.0 ml of a concentrated aqueous ammonia solution was added. Following agitation at room temperature overnight, the resultant was subjected to extraction with ethyl acetate/water. The organic layer was washed with saturated saline and then sodium sulfate was added for drying. The organic layer was subjected to vacuum condensation, and the resulting residue was added with 100 mg of 10% Pd/C and 12.0 ml of methanol and stirred at room temperature overnight in a hydrogen atmosphere under a normal pressure. After the reaction, the catalyst was filtrated away and the solvent was distilled away to obtain a crude purified substance of the title compound.

Workup

  1. additionwas added
  2. customat room temperature
  3. customovernight
  4. extractionthe resultant was subjected to extraction with ethyl acetate/water
  5. washThe organic layer was washed with saturated saline
  6. additionsodium sulfate was added
  7. customfor drying
  8. customThe organic layer was subjected to vacuum condensation
  9. customAfter the reaction
  10. filtrationthe catalyst was filtrated away
  11. distillationthe solvent was distilled away
  12. customto obtain a crude
  13. custompurified substance of the title compound

Sources & evidence

ORD record
ord-56569bf578c34ccea39e1941dcba2a51
Source dataset
uspto-grants-2015_10
Patent number
US09150505B2

Reaction notes

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