HCID 86684774, 화합물 → HCID 66685241, 화합물

HRID 579208노트

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HRID 579208 반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:26]#[C:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:8][C:9]=1[N:10]1[C@H:15]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:14][O:13][C@H:12]([CH2:22][CH:23]=[O:24])[C:11]1=[O:25])=[O:4].[CH3:32][Mg+].[Br-]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:26]#[C:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:8][C:9]=1[N:10]1[C@H:15]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:14][O:13][C@H:12]([CH2:22][C@H:23]([OH:24])[CH3:32])[C:11]1=[O:25])=[O:4].[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:26]#[C:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:8][C:9]=1[N:10]1[C@H:15]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:14][O:13][C@H:12]([CH2:22][C@@H:23]([OH:24])[CH3:32])[C:11]1=[O:25])=[O:4]

참가 물질

5

반응물 2

HCID 86684774HCID 86684774, 화합물HCID 178418689HCID 178418689, 화합물

생성물 2

HCID 66683972HCID 66683972, 화합물수율 29%HCID 66685241HCID 66685241, 화합물수율 40.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-10 °C

실험 절차

To a solution of 3-[(2R,5R)-5-cyclohexyl-3-oxo-2-(2-oxo-ethyl)-morpholin-4-yl]-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester (1.9 g, 4.26 mmol, 1.0 equiv) in THF (200 mL) at −10° C., was added MeMgBr (1.85 mL, 3.0 M solution in THF, 5.54 mmol, 1.3 equiv). The resulting solution was stirred at −10° C. for 20 minutes. The reaction was quenched by addition of 3.0 N HCl aqueous solution until pH=1. The volatile solvent was removed under vacuum and the residue was partitioned between EtOAc (100 mL) and brine (5 mL). The separated organic layer was dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography [Et2O (2% EtOAc)/Heptane, 25% to 50%] to give 3-[(2R,5R)-5-Cyclohexyl-2-((R)-2-hydroxy-propyl)-3-oxo-morpholin-4-yl]-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester (0.57 g, 29.0%) and 3-[(2R,5R)-5-Cyclohexyl-2-((S)-2-hydroxy-propyl)-3-oxo-morpholin-4-yl]-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester (0.80 g, 40.7%). MS: 462.4 [M−H+].

후처리

  1. customThe reaction was quenched by addition of 3.0 N HCl aqueous solution until pH=1
  2. customThe volatile solvent was removed under vacuum
  3. customthe residue was partitioned between EtOAc (100 mL) and brine (5 mL)
  4. dry with materialThe separated organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography [Et2O (2% EtOAc)/Heptane, 25% to 50%]

출처 및 근거

ORD 기록
ord-ecd8a7672bf740e69cb85edc9e9206a5
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040690B2

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