Piperidine → HCID 22093261, compound

HRID 393446Notes

Reaction equation

HRID 393446 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]([NH:11][C:12]1[CH:40]=[CH:39][C:15]([CH2:16][C@@H:17]([C:36]([OH:38])=[O:37])[NH:18]C(OCC2C3C=CC=CC=3C3C2=CC=CC=3)=O)=[CH:14][CH:13]=1)=[O:10].N1CCCCC1>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]([NH:11][C:12]1[CH:40]=[CH:39][C:15]([CH2:16][C@@H:17]([C:36]([OH:38])=[O:37])[NH2:18])=[CH:14][CH:13]=1)=[O:10]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 53670313HCID 53670313, compound

Product 1

HCID 22093261HCID 22093261, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To the 4-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanine on Wang resin prepared above (12.1 mmol, 17.4 g) was added 20% of piperidine in NMP at room temperature. The mixture was shaken for 1.5 h at room temperature and the resin was filtered and washed with DMF (2×20 mL). Then, the resin was suspended in 20% piperidine in NMP (100 mL) and the solvent was decanted. The resin was washed with dichloromethane (2×20 mL) and dried under high vacuum to obtain 13.5 g of 4-[[(2,6-dichlorophenyl)carbonyl]amino]-L-phenylalanine on Wang resin.

Workup

  1. filtrationthe resin was filtered
  2. washwashed with DMF (2×20 mL)
  3. customthe solvent was decanted
  4. washThe resin was washed with dichloromethane (2×20 mL)
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-b593cb51c516449d8f66e31529dee1a4
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

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