Piperidine → HCID 131732921, compound

HRID 2168837Notes

Reaction equation

HRID 2168837 reaction equation
C([NH:18][C@H:19]([C:31]([OH:33])=[O:32])[CH2:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1)(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.[NH2:34][C@H:35]([C:39]([O:41][CH2:42][CH:43]=[CH2:44])=[O:40])[CH:36]([CH3:38])[CH3:37].N1CCCCC1>C(Cl)Cl>[C:21]1([CH2:20][C@@H:19]([C:31]([OH:33])=[O:32])[NH2:18])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1.[NH2:34][C@H:35]([C:39]([O:41][CH2:42][CH:43]=[CH2:44])=[O:40])[CH:36]([CH3:38])[CH3:37]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 131732922HCID 131732922, compound

Product 1

HCID 131732921HCID 131732921, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Fmoc-3-(1-naphtyl)-L-alanine-Val-OAllyl (0.67 g, 1.16 mmol) was solvated in CH2Cl2 (5 mL) followed by addition of piperidine (0.920 mL). After 45 min, the mixture was evaporated to dryness and co-evaporated with CH2Cl2 (20 mL*2) followed with high vacuum (without heating) for 10 min to remove the excess of piperidine. The sample was purified on silica with a gradient of MeOH/CH2Cl2 (0 to 5%) to get 0.396 g of the desired compound.

Workup

  1. customthe mixture was evaporated to dryness and co-evaporated with CH2Cl2 (20 mL*2)
  2. temperaturefollowed with high vacuum (without heating) for 10 min
  3. customto remove the excess of piperidine
  4. customThe sample was purified on silica with a gradient of MeOH/CH2Cl2 (0 to 5%)

Sources & evidence

ORD record
ord-6f2357164e9f44bfbb2ea2e79a5052f0
Source dataset
uspto-grants-2015_06
Patent number
US09045524B2

Reaction notes

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