Hydrochloric Acid → {(2S,4R)-1-[(1S,4R)-5-(Benzyloxy)-4-methyl-1-(3,3,3-trifluoropropyl)pent-2-yn-1-yl]-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetic acid

HRID 1942303노트

반응식

HRID 1942303 반응식
[OH-].[Li+].[CH2:3]([O:10][CH2:11][CH:12]([CH3:43])[C:13]#[C:14][C@@H:15]([N:22]1[CH2:27][CH2:26][C@@H:25]([CH2:28][C:29]([O:31]C)=[O:30])[CH2:24][C@H:23]1[C:33]1[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=1)[CH2:16][CH2:17][C:18]([F:21])([F:20])[F:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.C([O-])(O)=O.[Na+]>O.C1COCC1>[CH2:3]([O:10][CH2:11][C@H:12]([CH3:43])[C:13]#[C:14][C@@H:15]([N:22]1[CH2:27][CH2:26][C@@H:25]([CH2:28][C:29]([OH:31])=[O:30])[CH2:24][C@H:23]1[C:33]1[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:40])[F:41])=[CH:35][CH:34]=1)[CH2:16][CH2:17][C:18]([F:21])([F:20])[F:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 516892Sodium BicarbonateHCID 59201240Methyl {(2S,4R)-1-[(1S)-5-(benzyloxy)-4-methyl-1-(3,3,3-trifluoropropyl)pent-2-yn-1-yl]-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetate

생성물 1

HCID 86639340{(2S,4R)-1-[(1S,4R)-5-(Benzyloxy)-4-methyl-1-(3,3,3-trifluoropropyl)pent-2-yn-1-yl]-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetic acid수율 97.4%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of lithium hydroxide (19.7 mg, 0.822 mmol) in water (1 ml) was added to a stirred solution of the ester (Step 3, 96 mg, 0.164 mmol) in THF (2 ml) at RT. The mixture was stirred at RT o/n. 2N HCl (1 ml) was added The pH of the aqueous layer was adjusted to 7 with NaHCO3 (aq). The aqueous layer was extracted with DCM (×3). The combined extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (silica, 2-5% MeOH/DCM) to give the acid (91 mg) as a colourless oil. M/Z 570 (MH+).

후처리

  1. extractionThe aqueous layer was extracted with DCM (×3)
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by chromatography (silica, 2-5% MeOH/DCM)

출처 및 근거

ORD 기록
ord-c3d065db92cc477e96bcba140c4e7388
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389547B2

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