4-Methylmorpholine → HCID 67004356, 화합물

HRID 1919176노트

반응식

HRID 1919176 반응식
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[CH:7]=1)=[O:5].[C:13]([C:16]([CH2:23][Br:24])([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])(O)=[O:14].CN1CCOCC1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C1COCC1>[Br:24][CH2:23][C:16]([O:17][CH2:18][CH3:19])([O:20][CH2:21][CH3:22])[C:13]([NH:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[CH:7]=1)=[O:5])=[O:14]

참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 2724699PyBOPHCID 30262702-amino-1-(3-bromophenyl)ethanone hydrochlorideHCID 130997963-Bromo-2,2-diethoxypropanoic acid

생성물 1

HCID 67004356HCID 67004356, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The 2-amino-1-(3-bromophenyl)ethanone hydrochloride (4.6 g, 19 mmol), HO2CC(OEt)2CH2Br (5.0 g, 21 mmol), and NMM (12.5 mL, 113 mmol) were suspended in anhyd THF (270 mL) under N2 and PyBOP (10.8 g, 21 mmol) was added in one portion. The reaction mixture was stirred for 18 h and concentrated to ¼ vol and the precipitates were removed by filtration (HCl salt of NMM). The mother liquor was taken up in dichloromethane and washed with water. After concentration, the crude residue was subjected to flash chromatography (silica gel) eluting with 60% EtOAc/hexanes to give Intermediate J.1, 5.3 g (65%). 1H NMR (500 MHz, DMSO-d6): δ 8.27 (t, J=5.5 Hz, 1H), 8.14 (t, J=1.5 Hz, 1H), 8.00 (dt, J=7.9, 1.2 Hz, 1H), 7.87 (dd, J=8.8, 1.8 Hz, 1H), 7.51 (t, J=7.9 Hz, 1H), 4.65 (d, J=5.8 Hz, 2H), 3.67 (s, 2H) 3.58-3.46 (m, 4H), 1.18 (t, J=7.0 Hz, 6H). LCMS: 2.2 min; LRMS: Calcd. for C15H19Br2NO4: 435.98. Found: 435.98 (M+H)+.

후처리

  1. concentrationconcentrated
  2. customthe precipitates were removed by filtration (HCl salt of NMM)
  3. washwashed with water
  4. concentrationAfter concentration
  5. washeluting with 60% EtOAc/hexanes
  6. customto give Intermediate J.1, 5.3 g (65%)
  7. custom2.2 min

출처 및 근거

ORD 기록
ord-331ce07056b0446ba4719a54067e61c9
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618153B2

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