1,1'-Carbonyldiimidazole → Efavirenz

HRID 389413

反応式

HRID 389413 の反応式
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([C@@:9]([OH:19])([C:14]#[C:15][CH:16]2[CH2:18][CH2:17]2)[C:10]([F:13])([F:12])[F:11])[CH:3]=1.[C:20](N1C=CN=C1)(N1C=CN=C1)=[O:21]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]2[NH:6][C:20](=[O:21])[O:19][C@:9]([C:14]#[C:15][CH:16]3[CH2:18][CH2:17]3)([C:10]([F:12])([F:13])[F:11])[C:4]=2[CH:3]=1

参加物

4

反応物 2

HCID 682631,1'-CarbonyldiimidazoleHCID 11033574Efavirenz aminoalcohol

生成物 1

HCID 64139Efavirenz

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of (S)-4-chloro-2-(4-cyclopropyl-1,1,1-trifluoro-2-hydroxybut-3-yn-2-yl)aniline (4.42 g, 15.3 mmol), 1,1′-carbonyl diimidazole and toluene (50 mL) was stirred at room temperature for 10 minutes. The reaction was quenched with ice-water (10 mL). The two layers were separated, ethyl acetate (10 mL) was added to the toluene layer and the mixture was washed with brine (2×30 mL) and the two layers were separated. The organic layer was evaporated to dryness to give an orange oil and further crystallized with hexanes to give (S)-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one as a white or off-white solid. 1H NMR (CDCl3) δ 9.64 (s, 1H), 7.49 (a, s, 1H), 7.36 (dd, J=8.4, 1.8 Hz, 1H), 6.87 (d, J=8.4 Hz, 1H), 1.43-1.36 (m, 1H), 0.97-0.91 (m, 2H), 0.88-0.86 (m, 2H).

後処理

  1. customThe reaction was quenched with ice-water (10 mL)
  2. customThe two layers were separated
  3. additionethyl acetate (10 mL) was added to the toluene layer
  4. washthe mixture was washed with brine (2×30 mL)
  5. customthe two layers were separated
  6. customThe organic layer was evaporated to dryness
  7. customto give an orange oil
  8. customfurther crystallized with hexanes

出典と根拠

ORDレコード
ord-bb1ad4e0d6894aa6b5e576932b76ef4c
出典データセット
uspto-grants-2013_02
特許番号
US08378143B2

関連ノート

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