Water → HCID 15616710, 화합물

HRID 1383222

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HRID 1383222 반응식
[CH3:1][CH:2]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[NH:5]1)[CH3:3].C([Li])CCC.[CH:15]1([CH:18]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[C:19](Cl)=[O:20])[CH2:17][CH2:16]1.O>O1CCCC1>[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([CH:18]([CH:15]2[CH2:17][CH2:16]2)[C:19]([N:5]2[C@@H:4]([CH:2]([CH3:3])[CH3:1])[CH2:8][O:7][C:6]2=[O:9])=[O:20])=[CH:27][CH:26]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 7157133(4S)-4-(propan-2-yl)-1,3-oxazolidin-2-oneHCID 15083505alpha-Cyclopropyl-4-chlorophenylacetyl chlorideHCID 178418339Butyllithium

생성물 1

HCID 15616710HCID 15616710, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

In a separate reaction vessel a stirred solution of 2.0 grams (0.016 mole) of (S)-4-(1-methylethyl)-2-oxazolidinone in 50 mL of tetrahydrofuran was cooled to -78° C., and 6.25 mL (0.016 mole) of n-butyllithium (2.5 molar in hexane) was added dropwise. Upon completion of addition, the reaction mixture was stirred for 30 minutes, and then the 2-cyclopropyl-2-(4-chlorophenyl)acetyl chloride, prepared above, was added dropwise during several minutes. Upon completion of addition, the reaction mixture was stirred for an additional 30 minutes and then was poured into water. The organic layer was separated and washed with one portion of aqueous sodium bicarbonate. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil. The oil was subjected to chromatography on silica gel using hexane:diethyl ether (3:1) as eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 0.85 gram of diastereomer (A) and 0.8 gram of diastereomer (B) of (S)-N-[2-(4-chlorophenyl)-2-cyclopropylacetyl]-4-(1-methylethyl)-2-oxazolidinone. Upon standing, diastereomer (A) crystallized to a solid, m.p. 61°-64° C.

후처리

  1. additionUpon completion of addition
  2. additionwas added dropwise during several minutes
  3. additionUpon completion of addition
  4. stirringthe reaction mixture was stirred for an additional 30 minutes
  5. customThe organic layer was separated
  6. washwashed with one portion of aqueous sodium bicarbonate
  7. dry with materialThe organic layer was dried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure to a residual oil
  10. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-a711fc8fb4b34bcca3fdac245377932c
출처 데이터셋
uspto-grants-1989_02
특허 번호
US04808762

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