Sodium Hydroxide → (E)-3-{1'-tert-butoxycarbonyl-4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid

HRID 2046710노트

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HRID 2046710 반응식
[OH-].[Na+].C[O:4][C:5](=[O:31])/[CH:6]=[CH:7]/[C:8]1[CH:9]=[C:10]2[C:27](=[CH:28][CH:29]=1)[O:26][C:13]1([CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1)[CH2:12][C:11]2=[O:30]>O.CO>[C:22]([O:21][C:19]([N:16]1[CH2:17][CH2:18][C:13]2([CH2:12][C:11](=[O:30])[C:10]3[C:27](=[CH:28][CH:29]=[C:8](/[CH:7]=[CH:6]/[C:5]([OH:31])=[O:4])[CH:9]=3)[O:26]2)[CH2:14][CH2:15]1)=[O:20])([CH3:25])([CH3:23])[CH3:24]

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 52952087(E)-3-{1'-tert-butoxycarbonyl-4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid methyl ester2회

생성물 1

HCID 52952089(E)-3-{1'-tert-butoxycarbonyl-4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid수율 92%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

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온도
50 °C

실험 절차

NaOH (160 mg, 4 mmol) in H2O (2 ml) was added to a suspension of (E)-3-{1′-tert-butoxycarbonyl-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (462 mg, 1.15 mmol, Intermediate 1, Step B) in MeOH (6 ml). The mixture was stirred at 50° C. After 2 h, MeOH was evaporated and the pH of the aqueous phase was adjusted with 1 M HCl to a pH value of 5. The resulting suspension was extracted with DCM, the organic phase dried over Na2SO4 and concentrated to give (E)-3-{1′-tert-butoxycarbonyl-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid (410 mg) as a white solid.

후처리

  1. customMeOH was evaporated
  2. extractionThe resulting suspension was extracted with DCM
  3. dry with materialthe organic phase dried over Na2SO4
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8f1d6ed5c861485fbcf07de912817653
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592444B2

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