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Water → p-toluenesulphonic acid (4S,5S)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl ester

HRID 1901966
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인쇄 미리보기

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HRID 1901966 반응식
C(N(CC)CC)C.[CH2:8]([C@H:15]1[C@@H:19]([CH2:20][OH:21])[O:18][C:17](=[O:22])[NH:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.O>CC(C)=O>[CH2:8]([C@H:15]1[C@@H:19]([CH2:20][O:21][S:29]([C:26]2[CH:27]=[CH:28][C:23]([CH3:33])=[CH:24][CH:25]=2)(=[O:31])=[O:30])[O:18][C:17](=[O:22])[NH:16]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 9859125(4S,5S)-5-hydroxymethyl-4-phenylmethyloxazolidinone

생성물 1

HCID 56996730p-toluenesulphonic acid (4S,5S)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl ester수율 93.9%

시약·촉매·용매 1

HCID 180
Acetone
용매

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온도
22 °C

실험 절차

5.6 ml of triethylamine are added at 22° C. to a stirred suspension of 5.55 g of the alcohol from Example 8 in 27 ml of acetone and 6.64 g of p-toluenesulphonyl chloride and stirred at 22° C. for 6.5 hours. The suspension is treated with water, stirred at 10° C., filtered, the residue is washed with a water/acetone solution (3:2) and dried to give 9.09 g (94%) of 99% p-toluenesulphonic acid (4S,5S)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl ester, m.p. 148.7°-150.3° C., [α]D20 : +3.0° (1% acetone).

후처리

  1. stirringstirred at 10° C.
  2. filtrationfiltered
  3. washthe residue is washed with a water/acetone solution (3:2)
  4. customdried

출처 및 근거

ORD 기록
ord-487ed261c47f4970bbac912c21f665fa
출처 데이터셋
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05578730

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