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Carbon tetrabromide → (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(bromomethyl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one

HRID 505259
ノート
印刷プレビュー

反応式

HRID 505259 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:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3[CH2:30]O)[C@H:14]2[CH3:32])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(Br)(Br)(Br)[Br:36].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[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:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3[CH2:30][Br:36])[C@H:14]2[CH3:32])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[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

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 86628752(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(hydroxymethyl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one

生成物 1

HCID 57617862(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(bromomethyl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
2 回

実験手順

To a 0° C. solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(hydroxymethyl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one (210 mg, 0.419 mmol) in CH2Cl2 (4 mL) was added CBr4 (292 mg, 0.880 mmol) and a solution of PPh3 (220 mg, 0.838 mmol) in CH2Cl2 (4 mL). The mixture was allowed to warm to room temperature, and, after 90 minutes had elapsed, it was concentrated on to silica gel. Purification of the residue by flash chromatography on silica gel (10 to 50% EtOAc/hexanes) afforded (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(bromomethyl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one. Rf=0.10 (50% EtOAc/hexanes). LCMS=564.0 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.88 (s, 1H), 7.78 (s, 2H), 7.63-7.57 (m, 2H), 7.52 (s, 1H), 5.79 (d, J=8.0 Hz, 1H), 5.09 (d, J=15.8 Hz, 1H), 4.61 (dd, J=13.8, 10.5 Hz, 2H), 4.27 (d, J=15.8 Hz, 1H), 4.06-1.00 (m, 1H), 0.82 (d, J=6.4 Hz, 3H).

後処理

  1. concentrationit was concentrated on to silica gel
  2. customPurification of the residue by flash chromatography on silica gel (10 to 50% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-aefb59cd06c6417cb828c3e019c9d8ee
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

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