alpha-t-Butyloxycarbonylamino-alpha-[2-(trichloroethoxycarbonylamino)thiazol-4-yl)acetic acid ethyl ester → alpha-t-Butyloxycarbonylamino-alpha-(2-aminothiazol-4-yl)acetic acid ethyl ester

HRID 866450ノート

反応式

HRID 866450 の反応式
[CH2:1]([O:3][C:4](=[O:28])[CH:5]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:6]1[N:7]=[C:8]([NH:11]C(OCC(Cl)(Cl)Cl)=O)[S:9][CH:10]=1)[CH3:2]>C(O)=O.[Zn]>[CH2:1]([O:3][C:4](=[O:28])[CH:5]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:6]1[N:7]=[C:8]([NH2:11])[S:9][CH:10]=1)[CH3:2]

参加物

4

反応物 1

HCID 12763205alpha-t-Butyloxycarbonylamino-alpha-[2-(trichloroethoxycarbonylamino)thiazol-4-yl)acetic acid ethyl ester

生成物 1

HCID 12763199alpha-t-Butyloxycarbonylamino-alpha-(2-aminothiazol-4-yl)acetic acid ethyl ester収率 71.2%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 284Formic Acid溶媒

実験手順

To a solution of 2.80 g of α-t-butyloxycarbonylamino-α-[2-(trichloroethoxycarbonylamino)thiazol-4-yl)acetic acid ethyl ester in 60 ml of 90% formic acid is added 2.80 g of zinc dust under cooling and stirring. The mixture is stirred for 1 hour and zinc dust is filtered off. The filtrate is poured into water and the resultant solution is extracted with ethyl acetate. The organic layer is washed with saturated sodium bicarbonate aq. solution and then water, and dried over anhydrous magnesium sulfate. The distillation of the solvent gives 1.26 g (yield, 71.2%) of α-t-butyloxycarbonylamino-α-(2-aminothiazol-4-yl)acetic acid ethyl ester as crystals. Melting point: 143°-144° C.

後処理

  1. temperatureunder cooling
  2. stirringThe mixture is stirred for 1 hour
  3. filtrationzinc dust is filtered off
  4. additionThe filtrate is poured into water
  5. extractionthe resultant solution is extracted with ethyl acetate
  6. washThe organic layer is washed with saturated sodium bicarbonate aq. solution
  7. dry with materialwater, and dried over anhydrous magnesium sulfate
  8. distillationThe distillation of the solvent

出典と根拠

ORDレコード
ord-642542bfb07b4294afde9c13fadca21a
出典データセット
uspto-grants-1978_07
特許番号
US04098888

反応ノート

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