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

HRID 469479ノート

反応式

HRID 469479 の反応式
[S:1]1[CH:5]=[C:4]([CH:6]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=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.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1>C1COCC1>[S:1]1[CH:5]=[C:4]([CH:6]([NH:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=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 585569862-(Benzo[b]thiophen-3-yl)-2-(benzylamino)acetic acid

生成物 1

HCID 58557025(R)-quinuclidin-3-yl 2-(benzo[b]thiophen-3-yl)-2-(benzylamino)acetate収率 12.8%

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-(benzylamino)acetic acid (I37) (303 mg, 1.02 mmol), (R)-quinuclidin-3-ol (156 mg, 1.22 mmol), DCC (252 mg, 1.22 mmol), and HOBT (187 mg, 1.22 mmol) in dry THF (20 ml) was stirred at room temperature overnight. The solvent was evaporated, and the crude product was partitioned between EtOAc and 2M K2CO3. The organic phase was washed with 2M K2CO3 and brine, dried over Na2SO4, filtered and evaporated to dryness. The crude product was purified by flash chromatography (CH3CN/MeOH=8/2+0.2% NH4OH) to obtain (R)-quinuclidin-3-yl 2-(benzo[b]thiophen-3-yl)-2-(benzylamino)acetate (53 mg, 12.8% yield).

後処理

  1. customThe solvent was evaporated
  2. customthe crude product was partitioned between EtOAc and 2M K2CO3
  3. washThe organic phase was washed with 2M K2CO3 and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe crude product was purified by flash chromatography (CH3CN/MeOH=8/2+0.2% NH4OH)

出典と根拠

ORDレコード
ord-58919b11362448ba9ddd1eb45536928a
出典データセット
uspto-grants-2014_01
特許番号
US08629160B2

反応ノート

読み込み中…