Hydrochloric Acid → 2-t-Butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetic acid

HRID 462589ノート

反応式

HRID 462589 の反応式
[C:1]([O:5][C:6]([CH2:8][O:9][N:10]=[C:11]([C:15]1[N:16]=[C:17](N)[S:18][CH:19]=1)[C:12]([OH:14])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].N(OC(C)(C)C)=O.Cl.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O.C(OCC)(=O)C>[C:1]([O:5][C:6]([CH2:8][O:9][N:10]=[C:11]([C:15]1[N:16]=[CH:17][S:18][CH:19]=1)[C:12]([OH:14])=[O:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 11430Potassium CarbonateHCID 53395219HCID 53395219、化合物

生成物 1

HCID 544727372-t-Butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetic acid収率 55.8%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a suspension of 2-t-butoxycarbonylmethoxyimino-2-(2-aminothiazol-4-yl)acetic acid (syn isomer) (11.5 g) in tetrahydrofuran (80.5 ml) was added dropwise a solution of t-butyl nitrite (6.5 g) in tetrahydrofuran (32.5 ml) at 50° to 57° C. under stirring, and the mixture was stirred at 50° to 55° C. for 20 minutes. The reaction mixture was poured into a mixture of ethyl acetate and water and the solution was acidified to pH 1.0 with 10% hydrochloric acid. Water (60 ml) was added to the separated organic layer and the mixture was adjusted to pH 6.0 with 40% aqueous solution of potassium carbonate. The separated aqueous solution was washed with ethyl acetate and the solution was acidified to pH 2.8 with 10% hydrochloric acid. The acidified solution was extracted with ethyl acetate and the ethyl acetate layer was dried over magnesium sulfate and evaporated. The residue was triturated with diisopropyl ether to give 2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetic acid (syn isomer) (6.1 g), mp. 141° C. (dec.).

後処理

  1. stirringthe mixture was stirred at 50° to 55° C. for 20 minutes
  2. washThe separated aqueous solution was washed with ethyl acetate
  3. extractionThe acidified solution was extracted with ethyl acetate
  4. dry with materialthe ethyl acetate layer was dried over magnesium sulfate
  5. customevaporated
  6. customThe residue was triturated with diisopropyl ether

出典と根拠

ORDレコード
ord-c7eefe6f8c4544aab7e8b3c7e9f8be42
出典データセット
uspto-grants-1985_05
特許番号
US04515788

反応ノート

読み込み中…