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Water → 2-(4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetic acid

HRID 572352
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HRID 572352 반응식
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23]CC)=[O:22])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:26][C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[O:28])[CH2:6][C@@H:5]1[CH3:33])(=[O:3])[CH3:2].O.[OH-].[Na+]>CO>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:26][C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[O:28])[CH2:6][C@@H:5]1[CH3:33])(=[O:3])[CH3:2]
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참가 물질

5

반응물 3

HCID 962WaterHCID 14798Sodium Hydroxide2회HCID 68185396ethyl 2-(4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetate

생성물 1

HCID 529352352-(4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetic acid수율 79%

시약·촉매·용매 1

HCID 887
Methanol
용매

실험 절차

To a solution of ethyl {4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]phenyl}acetate (for a preparation see Intermediate 22) (270 mg, 0.597 mmol) in methanol (6 mL) and water (2.0 mL) was added aqueous sodium hydroxide (2N, 0.597 mL, 1.193 mmol) at room temperature and the resulting mixture was stirred for 6 h. Aqueous sodium hydroxide (2N, 0.5 mL) was added and the mixture was left standing overnight. The bulk of methanol was removed in vacuo and the resulting residue was partitioned between water and Et2O and the layers were separated. The aqueous layer was acidified with hydrochloric acid (2N, 2 mL) and extracted twice with EtOAc. The combined organic phases were dried over MgSO4 and concentrated in vacuo to give {4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]phenyl}acetic acid (200 mg, 0.471 mmol, 79% yield) as a brown foam. This compound was used in the next step without further purification. LCMS (HpH, 2 min), Rt=0.65, MH+=425.

후처리

  1. waitthe mixture was left
  2. waitstanding overnight
  3. customThe bulk of methanol was removed in vacuo
  4. customthe resulting residue was partitioned between water and Et2O
  5. customthe layers were separated
  6. extractionextracted twice with EtOAc
  7. dry with materialThe combined organic phases were dried over MgSO4
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-38f94058663e4ed299d1ce573842d617
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09029395B2

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