Benzoic Acid → (2R,4R,6R)-2-Methoxy-2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-6-(pent-4-enyl)-tetrahydro-2H-pyran-4-yl Benzoate

HRID 2251771노트

반응식

HRID 2251771 반응식
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.ClC1C=C(Cl)C=C(Cl)C=1C(Cl)=O.O[C@@H:32]1[CH2:37][C@@H:36]([CH2:38][CH2:39][CH2:40][CH:41]=[CH2:42])[O:35][C@:34]([C@@H:45]2[CH2:49][S:48][C:47](=[O:50])[N:46]2[CH2:51][C:52]2[CH:57]=[CH:56][C:55]([O:58][CH3:59])=[CH:54][CH:53]=2)([O:43][CH3:44])[CH2:33]1>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C.CCOCC>[C:1]([O:9][C@@H:32]1[CH2:37][C@@H:36]([CH2:38][CH2:39][CH2:40][CH:41]=[CH2:42])[O:35][C@@:34]([O:43][CH3:44])([C@@H:45]2[CH2:49][S:48][C:47](=[O:50])[N:46]2[CH2:51][C:52]2[CH:53]=[CH:54][C:55]([O:58][CH3:59])=[CH:56][CH:57]=2)[CH2:33]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 243Benzoic AcidHCID 81531DiisopropylethylamineHCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 59644055(R)-4-((2R,4R,6R)-4-Hydroxy-2-methoxy-6-(pent-4-enyl)-tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-one

생성물 1

HCID 59644040(2R,4R,6R)-2-Methoxy-2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-6-(pent-4-enyl)-tetrahydro-2H-pyran-4-yl Benzoate수율 81%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 1140Toluene용매HCID 3283Diethyl Ether용매

실험 절차

To a solution of benzoic acid (31.7 mg, 0.260 mmol) in dry toluene (5 mL) under a nitrogen atmosphere was added diisopropylethylamine (0.0435 mL, 0.250 mmol) and 2,4,6-trichlorobenzoyl chloride (0.0391 mL, 0.250 mmol). The mixture was stirred at room temperature for 3 h, after which the title compound from Example 14 (21.5 mg, 0.051 mmol) and DMAP (32.9 mg, 0.269 mmol) were added. This mixture was stirred at room temperature for 18 h, after which it was diluted with ether and washed with satd aq NH4Cl and brine, and the organic phase was dried and evaporated. Chromatography of the residue on silica gel, eluting with an ethyl acetate/dichloromethane gradient, afforded the title compound (21.7 mg, 81%) as an oil.

후처리

  1. stirringThis mixture was stirred at room temperature for 18 h
  2. washwashed with satd aq NH4Cl and brine
  3. customthe organic phase was dried
  4. customevaporated
  5. washChromatography of the residue on silica gel, eluting with an ethyl acetate/dichloromethane gradient

출처 및 근거

ORD 기록
ord-f001cfd244a04be3ac48749655f15b68
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07320974B2

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