Aldoxime → 3-[2-(3-Methyl-isoxazol-5-yl)-pyridin-4-yl]-3-oxo-propionic acid tert.-butyl ester

HRID 1266761

反応式

HRID 1266761 の反応式
CO[C:3](=[O:16])[C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]2[O:14][N:13]=[C:12]([CH3:15])[CH:11]=2)[CH:5]=1.COC(=O)C1C=CN=C(I)C=1.C[Si](C#C)(C)C.C([O-])([O-])=O.[K+].[K+].C1C(=O)N(Cl)C(=O)C1.C(=NO)C.[C:52]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])(=[O:54])[CH3:53].[Li]>CO.C(Cl)(Cl)Cl.N1C=CC=CC=1.CCN(CC)CC>[C:56]([O:55][C:52](=[O:54])[CH2:53][C:3]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]2[O:14][N:13]=[C:12]([CH3:15])[CH:11]=2)[CH:5]=1)=[O:16])([CH3:59])([CH3:58])[CH3:57]

参加物

12

反応物 7

HCID 7863AldoximeHCID 11430Potassium CarbonateHCID 31398ChlorosuccinimideHCID 66111TrimethylsilylacetyleneHCID 196869Methyl 2-iodoisonicotinateHCID 696879722-(3-Methyl-isoxazol-5-yl)-isonicotinic acid methyl esterHCID 86586795Lithium Tert-butyl Acetate

生成物 1

HCID 696881723-[2-(3-Methyl-isoxazol-5-yl)-pyridin-4-yl]-3-oxo-propionic acid tert.-butyl ester

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 1049Pyridine溶媒HCID 6212Chloroform溶媒HCID 8471Triethylamine溶媒

実験手順

The title compound was prepared from 2-(3-methyl-isoxazol-5-yl)-isonicotinic acid methyl ester [prepared by i.) reaction of 2-iodo-isonicotinic acid methyl ester [CAS-No. 134579-47-8] with trimethylsilylacetylene according to general procedure H; ii.) desilylation by reaction with cat. K2CO3 in MeOH at 0° C. for 4 h; iii.) cycloadditon with a mixture of NCS, acetaldoxime, Et3N and cat. amount of pyridine in CHCl3 at 50° C. according to Tetrahedron 1984, 40, 2985-2988] by treatment with lithium tert.-butyl acetate according to general procedure K (method b). Obtained as a brown solid (5.17 g). MS (EI) 302 (M+); mp 59-67° C.

後処理

  1. customprepared by i
  2. custom) desilylation by reaction with cat
  3. customat 50° C.

出典と根拠

ORDレコード
ord-ef5cac25bc4546ac88526305050890c8
出典データセット
uspto-grants-2003_04
特許番号
US06548495B2

関連ノート

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