Acetyl chloride → HCID 57228641, 화합물

HRID 974261노트

반응식

HRID 974261 반응식
[CH:1]1([CH2:4][NH:5][C:6]2[N:14]=[CH:13][N:12]=[C:11]3[C:7]=2[N:8]=[CH:9][N:10]3[C@H:15]2[CH2:19][CH2:18][C@@H:17]([CH2:20][OH:21])[O:16]2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:29](Cl)(=[O:31])[CH3:30]>CN(C)C1C=CN=CC=1.C(#N)C>[C:29]([O:21][CH2:20][C@H:17]1[O:16][C@@H:15]([N:10]2[CH:9]=[N:8][C:7]3[C:11]2=[N:12][CH:13]=[N:14][C:6]=3[NH:5][CH2:4][CH:1]2[CH2:2][CH2:3]2)[CH2:19][CH2:18]1)(=[O:31])[CH3:30]

참가 물질

6

반응물 3

HCID 6367Acetyl chloride2회HCID 8471Triethylamine2회HCID 18649770HCID 18649770, 화합물

생성물 1

HCID 57228641HCID 57228641, 화합물수율 52.5%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6342Acetonitrile용매

실험 절차

6-(Cyclopropylmethylamino)-9-[(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furyl]-9H-purine (0.290 g, 1 mmoles), 4-dimethylaminopyridine (10.2 mg, 0.1 mmoles, Aldrich Chemical Co., Madison, Wis.), and triethylamine (620 μl, 4.4 mmoles, Aldrich Chemical Co., Madison, Wis.) were dissolved in 50 mL acetonitrile. The flask was chilled in an ice bath and acetyl chloride (150 μl, 2.1 mmoles, Aldrich Chemical Co., Madison, Wis.) was added. The reaction was brought to room temperature and stirred for 4 hours. Additional aliquots of triethylamine (620 μl, 4.4 mmoles) and acetyl chloride (150 μl, 2.1 mmoles) were added and the reaction was stirred overnight. The reaction was quenched with methanol and solvents were evaporated in vacuo. The residue was suspended in 25 mL ethyl acetate and salts were removed by filtration. Solvent was evaporated in vacuo and the remaining material was chromatographed on a Chromatotron (4 mm silica gel plate) with a mixture of hexane:acetone (7:3). Lyophilization afforded 0.174 g of 9-[(2R,5S)-5-(acetoxymethyl)-tetrahydro-2-furyl]-6-(cyclopropylmethylamino)-9H-purine as an oil (51% yield).

후처리

  1. temperatureThe flask was chilled in an ice bath
  2. customwas brought to room temperature
  3. stirringthe reaction was stirred overnight
  4. customThe reaction was quenched with methanol and solvents
  5. customwere evaporated in vacuo
  6. customsalts were removed by filtration
  7. customSolvent was evaporated in vacuo
  8. customthe remaining material was chromatographed on a Chromatotron (4 mm silica gel plate) with a mixture of hexane:acetone (7:3)

출처 및 근거

ORD 기록
ord-ac38c2b48c8b491c8e207d505458ddbd
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05068320

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