Dicyclohexylcarbodiimide → HCID 46840422、化合物

HRID 469452ノート

反応式

HRID 469452 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].[N:21]12[CH2:28][CH2:27][CH:24]([CH2:25][CH2:26]1)[C@@H:23](O)[CH2:22]2.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1>C1COCC1>[O:13]=[C:12]([O:14][C@@H:23]1[CH:24]2[CH2:27][CH2:28][N:21]([CH2:26][CH2:25]2)[CH2:22]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 28%

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) (404 mg, 1.39 mmol), (R)-quinuclidin-3-ol (529 mg, 4.17 mmol), DCC (859 mg, 4.17 mmol) and HOBT (567 mg, 4.17 mmol) in dry THF (25 ml) was stirred at room temperature overnight. THF was evaporated, and the crude product was taken up with EtOAc and washed twice with 2M K2CO3. The organic phase was dried over Na2SO4, filtered and evaporated to dryness. The crude was purified by flash chromatography (DCM/MeOH=98/2 to 95/5) recovering diastereomer 1 of C11 (161 mg; 28% yield), and subsequently diastereomer 2 of C11 (127 g, 35% yield).

後処理

  1. customTHF was evaporated
  2. washwashed twice with 2M K2CO3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude was purified by flash chromatography (DCM/MeOH=98/2 to 95/5)
  7. customrecovering diastereomer 1 of C11 (161 mg; 28% yield), and subsequently diastereomer 2 of C11 (127 g, 35% yield)

出典と根拠

ORDレコード
ord-d6c56ec0ffe94cd9a15280369967b156
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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