Sulfuric Acid → (S)-methyl 2-(2-amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

HRID 510262ノート

反応式

HRID 510262 の反応式
[NH2:1][C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[C:9]([C@H:18]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:19]([OH:21])=[O:20])[C:8]([CH3:27])=[CH:7][C:5]=2[N:6]=1.OS(O)(=O)=O.[CH3:33]COC(C)=O.C([O-])(O)=O.[Na+]>CO>[NH2:1][C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[C:9]([C@H:18]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])[C:19]([O:21][CH3:33])=[O:20])[C:8]([CH3:27])=[CH:7][C:5]=2[N:6]=1

参加物

6

反応物 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 86699792(S)-2-(2-amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetic acid

生成物 1

HCID 86699793(S)-methyl 2-(2-amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of Preparation of (S)-2-(2-amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetic acid from above in MeOH (25 mL) was added H2SO4 (200 μL). The reaction mixture was stirred at rt overnight. EtOAc (20 mL) and saturated NaHCO3 solution (50 mL) were added. The layers were separated, dried, filtered, and concentrated in vacuo. The crude mixture was a mixture of the desired (S)-methyl 2-(2-amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate and (S)-methyl 2-(2-amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-hydroxyacetate. t-Butyl acetate was added (20 mL) and perchloric acid (500 μL). The mixture was stirred at rt for 3 hr, where all (S)-methyl 2-(2-amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-hydroxyacetate was converted to (S)-methyl 2-(2-amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate. EtOAc (10 mL) and saturated NaHCO3 solution (50 mL) were added. The layers were separated, dried, filtered, and concentrated in vacuo. LCMS-ESI+: calc'd for C21H23ClN2O3S: 419.1 and 421.1 (M+H+); found: 419.2 and 421.2 (M+H+).

後処理

  1. customThe layers were separated
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. additiona mixture of the desired (S)-methyl 2-(2-amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate and (S)-methyl 2-(2-amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-hydroxyacetate
  6. additiont-Butyl acetate was added (20 mL) and perchloric acid (500 μL)
  7. stirringThe mixture was stirred at rt for 3 hr
  8. additionEtOAc (10 mL) and saturated NaHCO3 solution (50 mL) were added
  9. customThe layers were separated
  10. customdried
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-5e3ba46abe6844f881b370aa926fe95f
出典データセット
uspto-grants-2015_08
特許番号
US09096586B2

反応ノート

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