Piperidine → HCID 12019599, compound

HRID 1596074Notes

Reaction equation

HRID 1596074 reaction equation
[CH3:1][O:2][C:3](=[O:53])[C@H:4]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:52])[C@H:26]([NH:34]C(OCC2C3C(=CC=CC=3)C3C2=CC=CC=3)=O)[CH2:27][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)=[CH:20][CH:19]=1)[NH:5][C:6]([C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:15][CH3:16])=[S:7].N1CCCCC1>CN1C(=O)CCC1.CCCCCC>[CH3:1][O:2][C:3](=[O:53])[C@H:4]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:52])[C@H:26]([NH2:34])[CH2:27][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)=[CH:20][CH:19]=1)[NH:5][C:6]([C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:15][CH3:16])=[S:7]

Participants

5

Reactant 2

HCID 8082PiperidineHCID 12042600HCID 12042600, compound

Product 1

HCID 12019599HCID 12019599, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

N-[(2-ethyl-6-methylphenyl)thioxomethyl]-4-[[(2R)-2-(Fmoc-amino)-1-oxo-3-(pyridin-3-yl)propyl]amino]-L-phenylalanine methyl ester from example 26 (0.308 mmol, 224 mg) was treated with 25% piperidine in NMP (3 mL) and the solution was stirred at room temperature. Within 1 h, TLC analysis of the mixture indicated the absence of starting material. The mixture was diluted with hexane (25 mL) and the formed layers were separated. The bottom yellow layer was washed with hexane, then was diluted with water and extracted with ethyl acetate and THF (2:1, 3×25 mL). The combined extracts were washed with water (50 mL), brine (50 mL), dried (MgSO4), filtered and the solvents were removed under vacuum. The resulting residue was dried under high vacuum to afford 126 mg (81%) of 4-[[(2R)-2-amino-1-oxo-3-(pyridin-3-yl)propyl]amino]-N-[(2-ethyl-6-methylphenyl)thioxomethyl]-L-phenylalanine methyl ester as an amorphous colorless solid. HR MS: Obs. mass, 505.2270. Calcd. mass, 505.2274 (M+H).

Workup

  1. customthe formed layers were separated
  2. washThe bottom yellow layer was washed with hexane
  3. additionwas diluted with water
  4. extractionextracted with ethyl acetate and THF (2:1, 3×25 mL)
  5. washThe combined extracts were washed with water (50 mL), brine (50 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvents were removed under vacuum
  9. customThe resulting residue was dried under high vacuum

Sources & evidence

ORD record
ord-0c3712fa1983439fa633f4f6ca19dd03
Source dataset
uspto-grants-2001_09
Patent number
US06288267B1

Reaction notes

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