Phosgene → (R,R)-3-[1-(3,4-dimethoxyphenyl)prop-2-yl]-5-(3-chlorophenyl)oxazolidin-2-one

HRID 129549노트

반응식

HRID 129549 반응식
COC1C=C(C=CC=1OC)[CH2:6][N:7]([C@H:18]([CH3:30])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=1)[CH2:8][CH:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)[OH:10].[H-].[Na+].C(N(CC)CC)C.C(Cl)(Cl)=[O:46]>C1(C)C=CC=CC=1>[CH3:29][O:28][C:22]1[CH:21]=[C:20]([CH2:19][C@H:18]([N:7]2[CH2:8][C@@H:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=3)[O:10][C:6]2=[O:46])[CH3:30])[CH:25]=[CH:24][C:23]=1[O:26][CH3:27]

참가 물질

6

반응물 4

HCID 6371PhosgeneHCID 8471TriethylamineHCID 24758Sodium hydrideHCID 67780529(R)-N-(3,4-dimethoxybenzyl)-N-[2-(3-chlorophenyl)-2-hydroxyeth-1-yl]-1-(3,4-dimethoxyphenyl)-prop-2-ylamine

생성물 1

HCID 9885973(R,R)-3-[1-(3,4-dimethoxyphenyl)prop-2-yl]-5-(3-chlorophenyl)oxazolidin-2-one

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

A solution of 0.8 g. of (R)-N-(3,4-dimethoxybenzyl)-N-[2-(3-chlorophenyl)-2-hydroxyeth-1-yl]-1-(3,4-dimethoxyphenyl)-prop-2-ylamine in 10 mL of toluene is added to a slurry of 64 mg. of sodium hydride (60% oil slurry) in 5 mL of toluene at room temperature. The reaction mixture is stirred for one hour, 0.11 mL of triethylamine is added, and the reaction mixture is stirred for an additional 30 minutes. A 1.93M solution of phosgene (0.9 mL) is added and the reaction mixture is stirred for one hour and quenched with 10% hydrochloric acid. Additional toluene is added and the mixture is sequentially washed with dilute hydrochloric acid, 3N sodium hydroxide, and brine, after which it is dried over magnesium sulfate and concentrated to yield (R,R)-3-[1-(3,4-dimethoxyphenyl)prop-2-yl]-5-(3-chlorophenyl)oxazolidin-2-one which is further purified by recrystallization from 1:7 ethanol:heptane to yield white crystals. Gas chromatography indicates the chemical purity is 99.9% and HPLC indicates the optical purity is 99.6%. 1H NMR (250 MHz, CDCl3) d 1.26 (d, 3H, J=6.7 Hz), 2.65-2.85 (m, 2H), 3.25 (m, 1H), 3.8-3.9 (m, 1H), 3.82 (s, 3H), 3.86 (s, 3H), 4.34 (m, 1H), 5.35 (m, 1H), 6.6-7.4 (m, 7H).

후처리

  1. customat room temperature
  2. stirringthe reaction mixture is stirred for an additional 30 minutes
  3. stirringthe reaction mixture is stirred for one hour
  4. customquenched with 10% hydrochloric acid
  5. additionAdditional toluene is added
  6. washthe mixture is sequentially washed with dilute hydrochloric acid, 3N sodium hydroxide, and brine
  7. dry with materialafter which it is dried over magnesium sulfate
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0e3597d1e05d4d49af69c866206e152e
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05468865

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