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Acetic Acid → 1-(4-p-Nitrobenzyloxycarbonyl-1,3-thiazol-2-yl)-3-hydroxyazetidine

HRID 891549
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HRID 891549 반응식
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=3)=[O:29])[N:27]=2)[CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[N+:38]([C:35]1[CH:36]=[CH:37][C:32]([CH2:31][O:30][C:28]([C:26]2[N:27]=[C:23]([N:21]3[CH2:22][CH:19]([OH:18])[CH2:20]3)[S:24][CH:25]=2)=[O:29])=[CH:33][CH:34]=1)([O-:40])=[O:39]
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참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 222427683-t-Butyldiphenylsilyloxy-1-(4-p-nitrobenzyloxycarbonyl-1,3-thiazol-2-yl)azetidine

생성물 1

HCID 222428971-(4-p-Nitrobenzyloxycarbonyl-1,3-thiazol-2-yl)-3-hydroxyazetidine수율 81%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매
2회

실험 절차

To a solution of 3-t-butyldiphenylsilyloxy-1-(4-p-nitrobenzyloxycarbonyl-1,3-thiazol-2-yl)azetidine (93 mg, 0.16 mmol) (obtained as described in Reference Example 2(5)) in anhydrous tetrahydrofuran (4.7 ml) were added acetic acid (0.028 ml, 0.49 mmol) and a solution of 1 M tetrabutylammonium fluoride in tetrahydrofuran (0.48 ml, 0.48 mmol) in an ice bath. The mixture was stirred for 2 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using toluene:acetonitrile (2:1) as the eluant to afford 1-(4-p-nitrobenzyloxycarbonyl-1,3-thiazol-2-yl)-3-hydroxyazetidine (42.4 mg, yield 81%) as a pale yellow solid.

후처리

  1. customthe completion of the reaction
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column

출처 및 근거

ORD 기록
ord-c7a39c70f409477c9b256c980aa1a7dc
출처 데이터셋
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07001897B2

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