Cesium carbonate → 4-Methoxybenzyl 2-[(3S,4S)-4-t-Butyldimethylsilyloxymethyl-2-oxo-3-tritylaminoazetidin-1-yl]acetate

HRID 1901446

반응식

HRID 1901446 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].[Si:7]([O:14][CH2:15][C@H:16]1[NH:19][C:18](=[O:20])[C@H:17]1[NH:21][C:22]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].Br[CH2:42][C:43]([O:45][CH2:46][C:47]1[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=1)=[O:44]>C(#N)C.CN(C)C=O>[Si:7]([O:14][CH2:15][C@H:16]1[N:19]([CH2:42][C:43]([O:45][CH2:46][C:47]2[CH:48]=[CH:49][C:50]([O:53][CH3:54])=[CH:51][CH:52]=2)=[O:44])[C:18](=[O:20])[C@H:17]1[NH:21][C:22]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 132332344-Methoxybenzyl 2-bromoacetateHCID 13859068(3S,4S)-4-t-Butyldimethylsilyloxymethyl-3-tritylaminoazetidinone

생성물 1

HCID 702000314-Methoxybenzyl 2-[(3S,4S)-4-t-Butyldimethylsilyloxymethyl-2-oxo-3-tritylaminoazetidin-1-yl]acetate수율 114.7%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매

실험 절차

Cesium carbonate (1.58 g) was added to a stirred solution of (3S,4S)-4-t-butyldimethylsilyloxymethyl-3-tritylaminoazetidin-2-one (1.45 g) (IV) (H. Mastalerz et al., J. Med. Chem., 1988, 31, 1190-1196) in a mixture of acetonitrile (44 ml) and dimethylformamide (35 ml). 4-Methoxybenzyl bromoacetate (1.44 g) was then added and the mixture stirred at room temperature for 48 h. The mixture was then partitioned between ethyl acetate and water, the organic phase was washed four times with water, and then with brine. The solution was dried over magnesium sulphate and evaporated. The title compound (2.29 g) was isolated by column chromatography of the residue (Silica gel, 3:1 hexane:ethyl acetate as eluent). [α]D21 -9.0°; νmax (CHCl3) 3352, and 1755 cm-1 ; δ(CDCl3) -0.04 (3H, s), 0.00 (3H, s), 0.88 (9H, s), 1.69 (1H, br s), 2.54 (1H, dd, J 3.33 and 11.68 Hz), 3.19 (1H, dd, J 2.05 and 11.68 Hz), 3.38 (1H, m), 3.51 (1H, d, J 17.98 Hz), 3.90 (3H, s), 4.46 (1H, d, J 17.98 Hz), 4.54 (1H, m), 5.06 (1H, d, J 11.79 Hz), 5.15 (1H, d, J 11.81 Hz), 6.94 (2H, d, J 8.68 Hz), 7.2-7.65 (17H, m).

후처리

  1. customThe mixture was then partitioned between ethyl acetate and water
  2. washthe organic phase was washed four times with water
  3. dry with materialThe solution was dried over magnesium sulphate
  4. customevaporated

출처 및 근거

ORD 기록
ord-7e08db2806d44960a7f2b5894ff09452
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05578591

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