Piperidine → HCID 86644624, compound

HRID 1662044Notes

Reaction equation

HRID 1662044 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:34]([NH:36][C@H:37]1[CH2:41][CH2:40][CH2:39][C@H:38]1[C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])=[O:35])[NH:16]C(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1CCCCC1>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:34]([NH:36][C@H:37]1[CH2:41][CH2:40][CH2:39][C@H:38]1[C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])=[O:35])[NH2:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 86644625HCID 86644625, compound

Product 1

HCID 86644624HCID 86644624, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of tert-butyl (1R,2S)-2-({N5-[(benzyloxy)carbonyl]-N2-[(9H-fluorene -9-ylmethoxy)carbonyl]-L-ornithyl}amino)cyclopentanecarboxylate (4.0 g) and chloroform(80 ml) was added piperidine (6.0 ml) under ice-cooling, followed by stirring at room temperature for 13 hours. The reaction mixture was washed with a saturated sodium bicarbonate solution, water, and saturated brine in this order, and the organic layer was dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1, and then 0→2→5% methanol/chloroform) to obtain tert-butyl (1R,2S)-2-({N5-[(benzyloxy)carbonyl]-L-ornithyl}amino)cyclopentanecarboxylate (2.6 g).

Workup

  1. temperaturecooling
  2. washThe reaction mixture was washed with a saturated sodium bicarbonate solution, water, and saturated brine in this order
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-9360029bba2248b1b59ca7aaeb4fc540
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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