Triphenylphosphine → HCID 59401133, 화합물

HRID 77053

반응식

HRID 77053 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 59401133HCID 59401133, 화합물수율 79.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-dc805f9e25c4444591a87322ff5bb48d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835682B2

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