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

HRID 648835ノート

反応式

HRID 648835 の反応式
[S:1]1[CH:5]=[C:4]([C:6](=O)[C:7]([OH:9])=[O:8])[N:3]=[CH:2]1.[NH2:11][O:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(=O)(O)[O-].[Na+].Cl.[Cl-].[Na+]>CO.O.C(OCC)(=O)C>[C:17]([O:16][C:14]([CH2:13][O:12][N:11]=[C:6]([C:4]1[N:3]=[CH:2][S:1][CH:5]=1)[C:7]([OH:9])=[O:8])=[O:15])([CH3:20])([CH3:19])[CH3:18]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 12919121tert-Butyl (aminooxy)acetateHCID 13187915HCID 13187915、化合物

生成物 1

HCID 544727372-t-Butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetic acid収率 66.8%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 2-(4-thiazolyl)glyoxylic acid (2.3 g) in methanol (23 ml) and t-butyl 2-aminooxyacetate (2.6 g) was stirred for an hour at ambient temperature. The reaction mixture was added to a mixture of ethyl acetate and water and adjusted to pH 7.5 with saturated aqueous solution of sodium bicarbonate. The separated aqueous layer was adjusted to pH 2.0 with 10% hydrochloric acid and the mixture was saturated sodium chloride. The acidic mixture was extracted with ethyl acetate. The extract layer was washed with saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated to give 2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetic acid (syn isomer) (2.8 g), mp. 136°-139° C.

後処理

  1. extractionThe acidic mixture was extracted with ethyl acetate
  2. washThe extract layer was washed with saturated aqueous solution of sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

出典と根拠

ORDレコード
ord-217fe107818444d2a981050eb046e194
出典データセット
uspto-grants-1988_04
特許番号
US04736039

反応ノート

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