Dicyclohexylcarbodiimide → HCID 46840422、化合物

HRID 469454ノート

反応式

HRID 469454 の反応式
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH:10][CH:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:12]([OH:14])=[O:13])=[O:4].N1(O)C2C=CC=CC=2N=N1.[N:31]12[CH2:38][CH2:37][CH:34]([CH2:35][CH2:36]1)[C@@H:33](O)[CH2:32]2.C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[O:13]=[C:12]([O:14][C@@H:33]1[CH:34]2[CH2:37][CH2:38][N:31]([CH2:36][CH2:35]2)[CH2:32]1)[CH:11]([NH:10][C:9]1[CH:8]=[CH:7][S:6][C:5]=1[C:3]([O:2][CH3:1])=[O:4])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 58557000HCID 58557000、化合物

生成物 1

HCID 46840422HCID 46840422、化合物収率 31.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 2-(2-(methoxycarbonyl)thiophen-3-ylamino)-2-phenylacetic acid (I10) (700 mg, 2.40 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (487 mg, 3.60 mmol), (R)-quinuclidin-3-ol (458 mg, 3.60 mmol), and DCC (744 mg, 3.60 mmol) in dry THF (20 ml) was stirred at room temperature overnight. THF was evaporated, the crude product was partitioned between DCM and 2M K2CO3. The organic phase was collected, dried over Na2SO4, filtered and evaporated to dryness. The crude was purified by flash-chromatography (DCM/MeOH=95/5) to obtain methyl 3-(2-oxo-1-phenyl-2-((R)-quinuclidin-3-yloxy)ethylamino)thiophene-2-carboxylate (302 mg, 31.4% yield).

後処理

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

出典と根拠

ORDレコード
ord-2e160929dda0454fa2c95fe8465242e1
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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