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Dichloromethane → 3-(4-(3(S)-Acetamidopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloro-ethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one

HRID 8163
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인쇄 미리보기

반응식

HRID 8163 반응식
Cl.[NH2:2][C@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]([C:29]4[CH:33]=[CH:32][O:31][N:30]=4)[C:21]([O:23][CH2:24][C:25]([Cl:28])([Cl:27])[Cl:26])=[O:22])[O:16][C:15]3=[O:34])=[CH:10][C:9]=2[F:35])[CH2:4]1.C(=O)(O)[O-].[Na+].ClCCl.[C:44](OC(=O)C)(=[O:46])[CH3:45]>O>[C:44]([NH:2][C@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]([C:29]4[CH:33]=[CH:32][O:31][N:30]=4)[C:21]([O:23][CH2:24][C:25]([Cl:28])([Cl:26])[Cl:27])=[O:22])[O:16][C:15]3=[O:34])=[CH:10][C:9]=2[F:35])[CH2:4]1)(=[O:46])[CH3:45]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 7918Acetic Anhydride2회HCID 516892Sodium BicarbonateHCID 695849253-(4(3(S) aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloroethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one hydrochloride salt

생성물 1

HCID 695847253-(4-(3(S)-Acetamidopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloro-ethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one
수율 83.7%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

3-(4-(3(S)-Aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloroethyl-oxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one hydrochloride salt (400 mg, 0.74 mM) was dissolved in water (5 ml) and treated with aqueous sodium bicarbonate solution (5 ml) and dichloromethane (10 ml) in an ice-bath. Acetic anhydride (216 mg, 2 mM) was added, the mixture stirred 18 hours, allowing the temperature to rise to ambient, followed by addition of a further portion of acetic anhydride (216 mg), and a further period of 10 hours stirring. The organic phase was separated, washed with aqueous sodium dihydrogen phosphate (2%, 2×15 ml), brine (10 ml), and dried (magnesium sulfate). Evaporation gave the desired product (338 mg).

후처리

  1. stirringa further period of 10 hours stirring
  2. customThe organic phase was separated
  3. washwashed with aqueous sodium dihydrogen phosphate (2%, 2×15 ml), brine (10 ml)
  4. dry with materialdried (magnesium sulfate)
  5. customEvaporation

출처 및 근거

ORD 기록
ord-193fe8c4c29b49618063ab36b76ee128
출처 데이터셋
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07087629B2

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