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Triethylamine → HCID 59485870, 화합물

HRID 1972197
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HRID 1972197 반응식
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C@H:16]([CH2:24][NH2:25])[O:15][C:14]3=[O:26])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[S:36](Cl)([CH3:39])(=[O:38])=[O:37]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C@H:16]([CH2:24][NH:25][S:36]([CH3:39])(=[O:38])=[O:37])[O:15][C:14]3=[O:26])=[CH:11][CH:12]=2)=[CH:27][CH:28]=1
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59485942HCID 59485942, 화합물

생성물 1

HCID 59485870HCID 59485870, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (4S,5S)-3-(4-(4-chlorophenoxy)phenyl)-5-(aminomethyl)-4-phenyl-oxazolidin-2-one (14 mg, 0.035 mmol) and triethylamine (0.01 mL, 0.07 mmol) in dichloromethane (0.4 mL) at 0° C. was added mesyl chloride (0.005 mL, 0.05 mmol). The reaction mixture was stirred for 10 min and was then quenched with saturated NaHCO3 aqueous solution. Water and dichloromethane was added and the organic was washed with brine, dried (MgSO4), and concentrated. Purification by prep-LC (10-90% Acetonitrile/water (0.05% ammonium acetate) gave 5 mg (31%). 1H NMR (acetone-d6) δ (ppm) 7.45-7.51 (m, 4H), 7.32-7.42 (m, 5H), 6.94-6.97 (m, 4H), 6.66 (t, 1H, J=6.6 Hz), 5.56 (d, 1H, J=5.6 Hz), 4.51, (dd, 1H, J=10.1, 4.7 Hz), 3.59-3.72 (m, 2H), 3.04 (s, 3H). HPLC-MS calculated C23H21ClN2O5S (M+H+): 473.1, found: 473.1.

후처리

  1. customwas then quenched with saturated NaHCO3 aqueous solution
  2. additionWater and dichloromethane was added
  3. washthe organic was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPurification by prep-LC (10-90% Acetonitrile/water (0.05% ammonium acetate)
  7. customgave 5 mg (31%)

출처 및 근거

ORD 기록
ord-49461c46b338422aa2770d79479cb1c6
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08431607B2

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