Methylamine → HCID 22879938, compound

HRID 1773097Notes

Reaction equation

HRID 1773097 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].Cl.[CH3:26][N:27](C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.CN.[H][H]>CN(C=O)C.CO.[Pd]>[C:2]([O:5][C:6]([NH:8][C@H:9]([C:22](=[O:24])[NH:27][CH3:26])[CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:1]

Participants

9

Reactant 5

HCID 6329MethylamineHCID 83589L-Glutamic acid, N-((1,1-dimethylethoxy)carbonyl)-, 5-(phenylmethyl) esterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 178418361HCID 178418361, compound

Product 1

HCID 22879938HCID 22879938, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

1010 mg (3 mmol) of Boc-Glu (OBzl)-OH, 600 mg (3.2 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 460 mg (3.1 mmol) of 1-hydroxybenzotriazole monohydrate were suspended in 12 ml of DMF, to which 300 μl (2.0 mmol) of a 40% aqueous methylamine solution was added. Following agitation at room temperature overnight, extraction was performed with ethyl acetate/water. The organic layer was washed with saturated saline, and the resultant was added with sodium sulfate for drying. The organic layer was subjected to vacuum condensation, and the resultant residue was dissolved in 10 ml of methanol, added with 100 mg of 10% Pd/C, and then stirred overnight in a hydrogen atmosphere. After the catalyst was filtrated away and the solvent was distilled away, purification step A was used to obtain a crude product of the title compound.

Workup

  1. additionwas added
  2. customat room temperature
  3. extractionovernight, extraction
  4. washThe organic layer was washed with saturated saline
  5. additionthe resultant was added with sodium sulfate
  6. customfor drying
  7. customThe organic layer was subjected to vacuum condensation
  8. filtrationAfter the catalyst was filtrated away
  9. distillationthe solvent was distilled away
  10. custompurification step A

Sources & evidence

ORD record
ord-29b6d635a6804d698ee96b75f917d4bc
Source dataset
uspto-grants-2016_02
Patent number
US09253997B2

Reaction notes

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