Acetyl chloride → HCID 57968771, 화합물

HRID 1471621노트

반응식

HRID 1471621 반응식
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:16]=[CH:15][C:10]3[B:11]([OH:14])[O:12][CH2:13][C:9]=3[CH:8]=2)=[CH:4][CH:3]=1.CCN(CC)CC.[C:26](Cl)(=[O:28])[CH3:27]>C(Cl)Cl>[OH:14][B:11]1[C:10]2[CH:15]=[CH:16][C:7]([O:6][C:5]3[CH:17]=[CH:18][C:2]([NH:1][C:26](=[O:28])[CH3:27])=[CH:3][CH:4]=3)=[CH:8][C:9]=2[CH2:13][O:12]1

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 57968840HCID 57968840, 화합물

생성물 1

HCID 57968771HCID 57968771, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a 20 mL scintillation vial containing 5-(4-amino-phenoxy)-3H-benzo[c][1,2]oxaborol-1-ol (68 mg, 0.28 mmol, 1.0 eq.) in DCM (3.0 mL) was added Et3N (47 μL, 0.33 mmol, 1.2 eq.), followed by acetyl chloride (22 μL, 0.31 mmol, 1.1 eq.). The mixture was stirred at room temperature overnight. The mixture was concentrated under reduced pressure. The residue was applied to silica chromatography eluting with MeOH/DCM (0:100 to 10:90) to give N-[4-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-5-yloxy)-phenyl]-acetamide as a white solid. LCMS (m/z) 284 (M+H); 1H NMR (DMSO-d6) δ: 10.17 (s, 1H), 7.68 (d, J=8.1 Hz, 1H), 7.58-7.63 (m, 2H), 6.94-6.99 (m, 2H), 6.88 (dd, J=8.0, 2.1 Hz, 1H), 6.84 (d, J=1.5 Hz, 1H), 4.85 (s, 2H), 3.12 (s, 1H), 2.00 (s, 3H).

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. washeluting with MeOH/DCM (0:100 to 10:90)

출처 및 근거

ORD 기록
ord-616b02feb6d8433ea1ed9bccb968f140
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012431B2

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