Triethylamine → HCID 86726296, compound

HRID 1422876Notes

Reaction equation

HRID 1422876 reaction equation
F[C:2](F)(F)[C:3]([O-])=O.[O:8]=[C:9]1[NH:14][C@@H:13]([C:15]([OH:17])=O)[CH2:12][CH2:11][CH2:10]1.C1CN([P+](ON2N=[N:42][C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][C:36]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN([CH2:56][CH3:57])CC.[CH2:58](Cl)Cl.[CH3:61][N:62]([CH:64]=[O:65])C>C(Cl)Cl>[C:61]1([NH:62][C:64]([C@@H:37]([NH:42][C:15]([C@H:13]2[CH2:12][CH2:11][CH2:10][C:9](=[O:8])[NH:14]2)=[O:17])[CH2:38][CH2:39][CH2:40][CH:41]=[CH2:36])=[O:65])[CH:3]=[CH:2][CH:57]=[CH:56][CH:58]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 84468TrifluoroacetateHCID 2724699PyBOPHCID 22350042dichloromethane N,N-dimethylformamideHCID 40424009(2R)-6-Oxopiperidine-2-carboxylic acid

Product 1

HCID 86726296HCID 86726296, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of DCM/DMF (10 ml, 10/2) of the trifluoroacetate salt obtained in Step A was reacted with (R)-6-oxo-piperidine-2-carboxylic acid (0.79 mmol) and PyBOP (0.79 mmol) in the presence of NEt3 (2.25 mmol) for 2 hours. The reaction mixture was diluted with DCM and washed with 5% Na2CO3, brine, 5% citric acid and brine. The organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude reaction mixture was purified through chromatography on silica gel using AcOEt/MeOH (9/1) as eluent to allow the desired adduct as a white solid.

Workup

  1. washwashed with 5% Na2CO3, brine, 5% citric acid and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude reaction mixture
  6. customwas purified through chromatography on silica gel

Sources & evidence

ORD record
ord-80767646b4974885bb2bdd15e5817c55
Source dataset
uspto-grants-2015_01
Patent number
US08927533B2

Reaction notes

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