ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

1,1-Dichloroethane → (4s,5r)-5-[3,5-Bis(trifluoromethyl)phenyl]-3-[2-[(diethylamino)methyl]-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one

HRID 505281
ノート
印刷プレビュー

反応式

HRID 505281 の反応式
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24]C=3C=O)[C@H]2C)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[NH:35]([CH2:38][CH3:39])[CH2:36][CH3:37].[BH-](OC(C)=O)(OC(C)=O)O[C:42]([CH3:44])=O.[Na+].Cl[CH:55](Cl)[CH3:56]>CCOC(C)=O>[F:1][C:2]([F:33])([F:34])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][C:37]=3[CH2:36][N:35]([CH2:42][CH3:44])[CH2:38][CH3:39])[C@H:55]2[CH3:56])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1
参加物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 63651,1-DichloroethaneHCID 8021DiethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 576178812-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethyl)benzaldehyde

生成物 1

HCID 24896004(4s,5r)-5-[3,5-Bis(trifluoromethyl)phenyl]-3-[2-[(diethylamino)methyl]-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethyl)benzaldehyde (14.5 mg, 0.0291 mmol) in dichloroethane (300 μL) was added HNEt2 (4.6 μL, 0.0436 mmol), and NaBH(OAc)3 (9.2 mg, 0.0436 mmol). The reaction was stirred at room temperature for 18 hours and then diluted with EtOAc (10 mL) and washed with brine (5 mL). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by PTLC (50% EtOAc/hexanes) afforded (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-[(diethylamino)methyl]-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one. Rf=0.57 (50% EtOAc/hexanes). LCMS=557.2 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.92 (s, 1H), 7.82 (s, 2H), 7.55-7.52 (m, 3H), 5.76 (d, J=8.0 Hz, 1H), 5.03 (d, J=16.1 Hz, 1H), 4.60 (d, J=16.1 Hz, 1H), 4.05-4.03 (m, 1H), 3.73 (d, J=13.5 Hz, 1H), 3.57 (d, J=13.7 Hz, 1H), 2.75-2.56 (m, 4H), 1.04 (bs, 6H), 0.80 (d, J=6.4 Hz, 3H).

後処理

  1. washwashed with brine (5 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the residue by PTLC (50% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-d0e9ea6bb19c4ed9a6dda3eef0e7310b
出典データセット
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07781426B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート