Trityl chloride → (Z)-alpha-((2-(tert-Butoxy)-1,1-dimethyl-2-oxoethoxy)imino)-2-(tritylamino)thiazol-4-acetic acid

HRID 323879ノート

反応式

HRID 323879 の反応式
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:11]/[O:12][C:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])([CH3:15])[CH3:14])/[C:8]([OH:10])=[O:9])[N:6]=1.C(N(CC)CC)C.[C:30]1([C:36]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)Cl)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl>[C:19]([O:18][C:16]([C:13]([O:12]/[N:11]=[C:7](/[C:5]1[N:6]=[C:2]([NH:1][C:36]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[S:3][CH:4]=1)\[C:8]([OH:10])=[O:9])([CH3:14])[CH3:15])=[O:17])([CH3:22])([CH3:21])[CH3:20]

参加物

5

反応物 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 6242497(alphaZ)-2-Amino-alpha-((2-(1,1-dimethylethoxy)-1,1-dimethyl-2-oxoethoxy)imino)-4-thiazoleacetic acid

生成物 1

HCID 11039088(Z)-alpha-((2-(tert-Butoxy)-1,1-dimethyl-2-oxoethoxy)imino)-2-(tritylamino)thiazol-4-acetic acid

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
22.5 °C

実験手順

To a suspension of (Z)-2-(2-aminothiazol-4-yl)-2-(2-tert-butoxycarbonylprop-2-oxyimino) acetic acid (monoblocked acid) (100 g) prepared as in Example 1 in methylene chloride (1.74 lt) is added triethylamine (33.76 g) slowly at 5-10° to obtain a clear solution. Add triphenylchloromethane (118.5 g) at 5-10° and then mass temperature is raised to 36-38°. The resulting reaction mixture is stirred for 6 hours. It is then cooled to 20-25° and washed with DM water. The organic layer is concentrated and toluene is added to the residue. The resulting slurry is cooled to 20-25° C., the product is filtered, washed with toluene and dried under reduced pressure at 40-45° C. Yield 171 g (98.5% of theory), water <0.2% w/w, assay 96-97% w/w, methylene chloride 2-2.5% w/w and toluene 1-2% w/w.

後処理

  1. customto obtain a clear solution
  2. customThe resulting reaction mixture
  3. temperatureIt is then cooled to 20-25°
  4. washwashed with DM water
  5. concentrationThe organic layer is concentrated
  6. additiontoluene is added to the residue
  7. filtrationthe product is filtered
  8. washwashed with toluene
  9. customdried under reduced pressure at 40-45° C

出典と根拠

ORDレコード
ord-76e064d125964f48a78c852410c2ef04
出典データセット
uspto-grants-2001_04
特許番号
US06214997B1

反応ノート

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