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Triethylamine → tert-butyl N-tert-butoxycarbonyl-N-[3-[3-[4-(chloromethyl)phenyl]isoxazol-5-yl]-5-(4-isopropylsulfonylphenyl)pyrazin-2-yl]carbamate

HRID 81377
ノート
印刷プレビュー

反応式

HRID 81377 の反応式
C(N(CC)CC)C.[C:8]([O:12][C:13]([N:15]([C:23]1[C:28]([C:29]#[CH:30])=[N:27][C:26]([C:31]2[CH:36]=[CH:35][C:34]([S:37]([CH:40]([CH3:42])[CH3:41])(=[O:39])=[O:38])=[CH:33][CH:32]=2)=[CH:25][N:24]=1)[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:14])([CH3:11])([CH3:10])[CH3:9].[Cl:43][CH2:44][C:45]1[CH:54]=[CH:53][C:48]([C:49](Cl)=[N:50][OH:51])=[CH:47][CH:46]=1>C(Cl)Cl>[C:8]([O:12][C:13]([N:15]([C:23]1[C:28]([C:29]2[O:51][N:50]=[C:49]([C:48]3[CH:53]=[CH:54][C:45]([CH2:44][Cl:43])=[CH:46][CH:47]=3)[CH:30]=2)=[N:27][C:26]([C:31]2[CH:32]=[CH:33][C:34]([S:37]([CH:40]([CH3:42])[CH3:41])(=[O:39])=[O:38])=[CH:35][CH:36]=2)=[CH:25][N:24]=1)[C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[O:14])([CH3:9])([CH3:10])[CH3:11]
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 8471TriethylamineHCID 59471983N,N-Di(Boc)-3-ethynyl-5-[4-(isopropylsulfonyl)phenyl]pyrazin-2-amineHCID 766866014-(Chloromethyl)-N-hydroxybenzimidoyl chloride

生成物 1

HCID 86680730tert-butyl N-tert-butoxycarbonyl-N-[3-[3-[4-(chloromethyl)phenyl]isoxazol-5-yl]-5-(4-isopropylsulfonylphenyl)pyrazin-2-yl]carbamate収率 83.8%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

Triethylamine (899.0 mg, 1.238 mL, 8.884 mmol) was added to a solution of tert-butyl N-tert-butoxycarbonyl-N-[3-ethynyl-5-(4-isopropylsulfonylphenyl)pyrazin-2-yl]carbamate 8 (4.05 g, 8.074 mmol) and 4-(chloromethyl)-N-hydroxy-benzimidoyl chloride (2.063 g, 8.494 mmol) in DCM (12 mL). The mixture was stirred at RT for 22 h then partitioned between DCM and an ice/water solution. The combined organic extract was dried over MgSO4 and concentrated under reduced pressure then purified by chromatography on silica gel (eluent 30-50% EtAc/petrol) yielding tert-butyl N-tert-butoxycarbonyl-N-[3-[3-[4-(chloromethyl)phenyl]isoxazol-5-yl]-5-(4-isopropylsulfonylphenyl)pyrazin-2-yl]carbamate as colourless crystals (4.53 g, 79%). 1H NMR (400 MHz, CDCl3) δ 1.41 (18H, s), 4.66 (2H, s), 7.37 (1H, s), 7.54 (2H, d, J=8.0 Hz), 7.90 (2H, d, J=8.0 Hz), 8.66 (1H, s)

後処理

  1. customthen partitioned between DCM
  2. extractionThe combined organic extract
  3. dry with materialwas dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customthen purified by chromatography on silica gel (eluent 30-50% EtAc/petrol)

出典と根拠

ORDレコード
ord-8b02f920e68d4b1aa48d8956a4a23089
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08846686B2

反応ノート

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