Dicyclohexylcarbodiimide → (R)-quinuclidin-3-yl 2-(benzo[b]thiophen-3-yl)-2-(3-fluorophenylamino)acetate

HRID 469481ノート

反応式

HRID 469481 の反応式
[S:1]1[CH:5]=[C:4]([CH:6]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[C:7]([OH:9])=[O:8])[C:3]2[CH:18]=[CH:19][CH:20]=[CH:21][C:2]1=2.[N:22]12[CH2:29][CH2:28][CH:25]([CH2:26][CH2:27]1)[C@@H:24](O)[CH2:23]2.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[S:1]1[CH:5]=[C:4]([CH:6]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[C:7]([O:9][C@@H:24]2[CH:25]3[CH2:28][CH2:29][N:22]([CH2:27][CH2:26]3)[CH2:23]2)=[O:8])[C:3]2[CH:18]=[CH:19][CH:20]=[CH:21][C:2]1=2

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 585569922-(Benzo[b]thiophen-3-yl)-2-(3-fluorophenylamino)acetic acid

生成物 1

HCID 58556987(R)-quinuclidin-3-yl 2-(benzo[b]thiophen-3-yl)-2-(3-fluorophenylamino)acetate収率 45.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 2-(benzo[b]thiophen-3-yl)-2-(3-fluorophenylamino)acetic acid (I40) (677 mg, 2.25 mmol), (R)-quinuclidin-3-ol (343 mg, 2.70 mmol), HOBT (413 mg, 2.70 mmol), and DCC (556 mg, 2.70 mmol) in THF (20 ml) was stirred at room temperature overnight. THF was evaporated, and the crude product was partitioned between EtOAc and 1M K2CO3. The organic phase was dried over Na2SO4, filtered and evaporated to dryness. The crude product was purified by flash chromatography (DCM/MeOH=98/2 to 95/5) to obtain (R)-quinuclidin-3-yl 2-(benzo[b]thiophen-3-yl)-2-(3-fluorophenylamino)acetate (421 mg, 45.6% yield over two steps).

後処理

  1. customTHF was evaporated
  2. customthe crude product was partitioned between EtOAc and 1M K2CO3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude product was purified by flash chromatography (DCM/MeOH=98/2 to 95/5)

出典と根拠

ORDレコード
ord-6dabe47da4814fea8907b15b5a86e5f0
出典データセット
uspto-grants-2014_01
特許番号
US08629160B2

反応ノート

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