Triphenylphosphine → HCID 59401133、化合物

HRID 1255086

反応式

HRID 1255086 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 59401133HCID 59401133、化合物収率 79.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-9bc76f026041427d85a93ef3e5255325
出典データセット
uspto-grants-2013_06
特許番号
US08455646B2

関連ノート

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