Triphenylphosphine → HCID 59401133, compound

HRID 1255086

Reaction equation

HRID 1255086 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C@H:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[N:19]12[CH2:26][CH2:25][CH:22]([CH2:23][CH2:24]1)[C@H:21](O)[CH2:20]2.CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[N:19]12[CH2:26][CH2:25][CH:22]([CH2:23][CH2:24]1)[C@@H:21]([O:11][C:10](=[O:12])[C@H:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:20]2

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 7364113-Quinuclidinol, (+)-HCID 5462977Diethyl azodicarboxylateHCID 7006576(R)-(4-fluoro-phenylamino)-phenyl-acetic acid

Product 1

HCID 59401133HCID 59401133, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-(4-fluoro-phenylamino)-phenyl-acetic acid (I253) (420 mg, 1.71 mmol) in dry THF (40 mL), are sequentially added (S)-quinuclidin-3-ol (218 mg, 1.71 mmol), DEAD (407 ul, 2.57 mmol) and triphenylphosphine (674 mg, 2.57 mmol). The reaction is refluxed for 30 minutes under N2 flowstream and then the solvent is evaporated. The residue is partitioned between water and EtOAc, the organic layer is separated, dried over Na2SO4, filtered and evaporated to dryness. The resulting crude is purified by flash chromatography (DCM/MeOH=95/5) to obtain the title compound as a pale yellow oil (480 mg, 79% yield).

Workup

  1. temperatureThe reaction is refluxed for 30 minutes under N2 flowstream
  2. customthe solvent is evaporated
  3. customThe residue is partitioned between water and EtOAc
  4. customthe organic layer is separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe resulting crude is purified by flash chromatography (DCM/MeOH=95/5)

Sources & evidence

ORD record
ord-9bc76f026041427d85a93ef3e5255325
Source dataset
uspto-grants-2013_06
Patent number
US08455646B2

Linked notes

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