Sodium Carbonate → tert-butyl N-(4-chloro-3-(hydroxymethyl)phenyl)carbamate

HRID 38673

반응식

HRID 38673 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:10])=[C:6]([CH2:8][OH:9])[CH:7]=1.[C:11](=[O:14])([O-])[O-:12].[Na+].[Na+]>O1CCOCC1.O>[Cl:10][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:11](=[O:14])[O:12][C:6]([CH3:8])([CH3:7])[CH3:5])=[CH:7][C:6]=1[CH2:8][OH:9]

참가 물질

5

반응물 2

HCID 10340Sodium CarbonateHCID 13567962(5-Amino-2-chlorophenyl)methanol

생성물 1

HCID 54223790tert-butyl N-(4-chloro-3-(hydroxymethyl)phenyl)carbamate수율 136.9%

시약·촉매·용매 2

HCID 962Water용매2회HCID 312751,4-Dioxane용매

실험 절차

To a solution of (5-amino-2-chlorophenyl)methanol (Aldrich, 500 mg, 3.17 mmol) in a mixture of dioxane (7.5 mL), water (7.5 mL) was added sodium carbonate (336 mg, 3.17 mmol) previously dissolved in 4 mL of water. Solution was stirred and cooled in an ice bath. Boc-anhydride (Aldrich, 692 mg, 3.17 mmol) was added in one portion, and stirring was continued at room temperature for 3 h. Dioxane was removed in vacuo conditions and the aqueous layer chilled, covered with a layer of ethyl acetate, and acidified to pH 4 with dilute KHSO4 (10%, aq) (ALDRICH). This was followed by extraction (EtOAc) and purification by chromatographic column 25 g cartridge (ISOLUTE silice) using Hex/EtOAc 100/0 to 50/50, giving 1,1-dimethylethyl [4-chloro-3-(hydroxymethyl)phenyl]carbamate (560 mg, 2.17 mmol, 68%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 9.46 (br s, 1H), 7.72 (s, 1H), 7.21-7.32 (m, 2H), 5.35 (t, 1H), 4.48 (d, 2H), 1.47 (s, 9H).

후처리

  1. temperaturecooled in an ice bath
  2. stirringstirring
  3. customDioxane was removed in vacuo conditions
  4. temperaturethe aqueous layer chilled
  5. extractionThis was followed by extraction (EtOAc) and purification by chromatographic column 25 g cartridge (ISOLUTE silice)

출처 및 근거

ORD 기록
ord-178c23a564744a40a216423d55993ca0
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524750B2

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