tert-Butanol → tert-butyl N-(1,3-thiazol-4-yl)carbamate

HRID 46293

反応式

HRID 46293 の反応式
[S:1]1[CH:5]=[C:4](C(O)=O)[N:3]=[CH:2]1.[C:9]([OH:13])([CH3:12])([CH3:11])[CH3:10].C([N:16]([CH2:19]C)CC)C.C1C=CC([O:27]P(OC2C=CC=CC=2)(N=[N+]=[N-])=O)=CC=1>>[C:9]([O:13][C:19](=[O:27])[NH:16][C:4]1[N:3]=[CH:2][S:1][CH:5]=1)([CH3:12])([CH3:11])[CH3:10]

参加物

5

反応物 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 3042714-Thiazolecarboxylic acid

生成物 1

HCID 53241636tert-butyl N-(1,3-thiazol-4-yl)carbamate収率 64.7%

実験手順

Thiazole-4-carboxylic acid (6.46 g, 50.0 mmol) was slurried in tert-butyl alcohol (280 mL, 2900 mmol). Triethylamine (7.68 mL, 55.1 mmol) and diphenylphosphonic azide (11.9 mL, 55.1 mmol) were added and the reaction was heated at reflux for 18 hours. The reaction was evaporated to a residue. The residue was dissolved in ethyl acetate and washed with water, 5% citric acid (aqueous), water, saturated aqueous sodium bicarbonate and brine. The organic phase was dried over magnesium sulfate and evaporated to a residue. The residue was purified by silica gel chromatography (80 g ISCO™ column, hexanes to ethyl acetate gradient elution). Product fractions were combined and evaporated to a residue. The residue was triturated with 20% methyl t-butyl ether in hexanes. The solid was collected by filtration. Vacuum drying gave 6.48 g of product as a white solid. LCMS Rt=1.46 minutes MS m/z 201 [MH]+

後処理

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 18 hours
  3. customThe reaction was evaporated to a residue
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water, 5% citric acid (aqueous), water, saturated aqueous sodium bicarbonate and brine
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. customevaporated to a residue
  8. customThe residue was purified by silica gel chromatography (80 g ISCO™ column, hexanes to ethyl acetate gradient elution)
  9. customevaporated to a residue
  10. customThe residue was triturated with 20% methyl t-butyl ether in hexanes
  11. filtrationThe solid was collected by filtration
  12. customVacuum drying

出典と根拠

ORDレコード
ord-ca7487c3868f4ad7b197979b3124fb1e
出典データセット
uspto-grants-2013_09
特許番号
US08541588B2

関連ノート

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