Triethylamine → 4-Piperidineacetic acid

HRID 1989880Notes

Reaction equation

HRID 1989880 reaction equation
Cl.C1([CH:8]([CH:12]2[CH2:17][CH2:16][N:15](C3C=CC(NC(C4C=CC=CC=4C4C=CC(C(F)(F)F)=CC=4)=O)=CC=3)[CH2:14][CH2:13]2)[C:9]([OH:11])=[O:10])C=CC=CC=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.OCC(OC)=O>C(Cl)Cl.O>[NH:15]1[CH2:16][CH2:17][CH:12]([CH2:8][C:9]([OH:11])=[O:10])[CH2:13][CH2:14]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 66774Methyl GlycolateHCID 2724699PyBOPHCID 68521936alpha-Phenyl-1-[4-[[[4'-(trifluoromethyl)[1,1'-biphenyl]-2-yl]carbonyl]amino]phenyl]-4-piperidineacetic acid monohydrochloride

Product 1

HCID 15125944-Piperidineacetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of intermediate (24) (0.000084 mol), PyBOP (0.00017 mol) and triethylamine (0.5 ml) in DCM (5 ml) was stirred for 60 minutes at room temperature. Methyl hydroxyacetate (0.0001 mol) was added and the reaction mixture was stirred for 3 hours at 40° C., then over the weekend at room temperature. Water (2 ml) was added. The mixture was stirred for 15 minutes, then filtered through Extrelut™ and the organic filtrate was evaporated. The residue was purified by HPLC. The product fractions were collected and the solvent was evaporated, yielding 4-piperidineacetic acid, α-phenyl-1-[4-[[[4′-(trifluoromethyl)[1,1′-biphenyl]-2-yl]carbonyl]amino]-phenyl]-, 2-methoxy-2-oxoethyl ester (compound 20).

Workup

  1. stirringthe reaction mixture was stirred for 3 hours at 40° C.
  2. customat room temperature
  3. stirringThe mixture was stirred for 15 minutes
  4. filtrationfiltered through Extrelut™
  5. customthe organic filtrate was evaporated
  6. customThe residue was purified by HPLC
  7. customThe product fractions were collected
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4d2601247c1b491ba72e2c8291340216
Source dataset
uspto-grants-2010_01
Patent number
US07642378B2

Reaction notes

Loading…