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Monobasic potassium phosphate → (6R,7R)-4-(tert-butoxycarbonyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-6-carboxylic acid

HRID 1022617
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HRID 1022617 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][C@H:10]2[CH:23]=[O:24])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl([O-])=[O:26].[Na+].P([O-])(O)(O)=O.[K+]>CC(=CC)C.C(O)(C)(C)C.C1COCC1.O.C(OCC)(=O)C>[C:19]([O:18][C:16]([N:12]1[CH2:11][C@@H:10]([C:23]([OH:26])=[O:24])[C@H:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[O:15][CH2:14][CH2:13]1)=[O:17])([CH3:20])([CH3:21])[CH3:22]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 3

HCID 516951Monobasic potassium phosphateHCID 23668197Sodium ChloriteHCID 86663853tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-formyl-1,4-oxazepane-4-carboxylate

생성물 1

HCID 66975341(6R,7R)-4-(tert-butoxycarbonyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-6-carboxylic acid수율 92%

시약·촉매·용매 5

HCID 962Water
용매
HCID 6386tert-Butanol용매
HCID 8028Tetrahydrofuran용매
HCID 8857Ethyl Acetate용매
HCID 105532-Methyl-2-butene용매

실험 절차

To a mixed solution of tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-formyl-1,4-oxazepane-4-carboxylate (7.3 g) in 2-methyl-2-butene (45 mL), tert-butanol (100 ml) and THF (100 ml) was added dropwise a solution of sodium chlorite (10.58 g) and potassium dihydrogenphosphate (16.38 g) in water (160 ml) under ice-cooling, and the mixture was stirred under ice-cooling for 2 hr. The reaction mixture was diluted with ethyl acetate. The diluted solution was washed with distilled water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (7.0 g).

후처리

  1. temperaturecooling
  2. temperaturecooling for 2 hr
  3. washThe diluted solution was washed with distilled water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-a2154aebb6c4485a92c9525bcfe0c84d
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08722662B2

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