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Acetic Acid → {[(3S,4R)-4-(4-chlorophenyl)-1-cyclopropylpyrrolidine-3-yl]carbonyl}-4-[(4,4-dimethylcyclohexyl)(2,2-dimethylpropanoyl)amino]-N,N-dimethyl-L-prolineamide HCl salt

HRID 1361338
ノート
印刷プレビュー

反応式

HRID 1361338 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][NH:11][CH2:10][C@H:9]2[C:13]([N:15]2[CH2:24][C@@H:23]([N:25]([CH:32]3[CH2:37][CH2:36][C:35]([CH3:39])([CH3:38])[CH2:34][CH2:33]3)[C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:22][C@H:16]2[C:17]([N:19]([CH3:21])[CH3:20])=[O:18])=[O:14])=[CH:4][CH:3]=1.C(O[C:43]1(O[Si](C)(C)C)[CH2:45][CH2:44]1)C.[Na].C([BH3-])#N.C(O)(=O)C>ClCCCl>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][N:11]([CH:43]3[CH2:45][CH2:44]3)[CH2:10][C@H:9]2[C:13]([N:15]2[CH2:24][CH:23]([N:25]([CH:32]3[CH2:37][CH2:36][C:35]([CH3:39])([CH3:38])[CH2:34][CH2:33]3)[C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:22][C@H:16]2[C:17]([N:19]([CH3:21])[CH3:20])=[O:18])=[O:14])=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 176Acetic AcidHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 24826348(4S)-1-[(3S,4R)-4-(4-chlorophenyl)pyrrolidine-3-yl]carbonyl-4-[(4,4-dimethylcyclohexyl)(2,2-dimethylpropanoyl)amino]-N,N-dimethyl-L-prolineamideHCID 131717404HCID 131717404、化合物

生成物 1

HCID 86636656
{[(3S,4R)-4-(4-chlorophenyl)-1-cyclopropylpyrrolidine-3-yl]carbonyl}-4-[(4,4-dimethylcyclohexyl)(2,2-dimethylpropanoyl)amino]-N,N-dimethyl-L-prolineamide HCl salt

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
80 °C

実験手順

To a solution of (4S)-1-[(3S,4R)-4-(4-chlorophenyl)pyrrolidine-3-yl]carbonyl-4-[(4,4-dimethylcyclohexyl)(2,2-dimethylpropanoyl)amino]-N,N-dimethyl-L-prolineamide (100 mg, 0.18 mmol) prepared in Example E1-1 in DCE (5 ml) was added 1-ethoxycyclopropoxytrimethylsilane (47 mg, 0.27 mmol) and sodium-cyanoborohydride (23 mg, 0.36 mmol), added a catalytic amount of acetic acid, and the solution was stirred at 80° C. for 2 h. After the reaction finished, the solvent was concentrated in vacuo, and extracted with a saturated NaHCO3 aqueous solution and EtOAc. The organic solution was dried over MgSO4, concentrated in vacuo, and the residue was purified by HPLC. This TFA salt of the compound was treated according to the procedure described in Step G of Example A1 to give the title compound.

後処理

  1. concentrationthe solvent was concentrated in vacuo
  2. extractionextracted with a saturated NaHCO3 aqueous solution and EtOAc
  3. dry with materialThe organic solution was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified by HPLC
  6. additionThis TFA salt of the compound was treated

出典と根拠

ORDレコード
ord-f4a740d2771640f2a02dd3b7ac9df09c
出典データセット
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07879852B2

反応ノート

読み込み中…

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