Cyclooctanone → HCID 20794995, 화합물

HRID 1070566

반응식

HRID 1070566 반응식
[C:1]([CH:5]([C:12]([OH:14])=[O:13])[CH2:6][C@@H:7]([C:9]([OH:11])=[O:10])[NH2:8])([CH3:4])([CH3:3])[CH3:2].[C:15]1(=O)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C)C=O.C(O)(=O)C>[CH:15]1([NH:8][C@H:7]([C:9]([OH:11])=[O:10])[CH2:6][CH:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:12]([OH:14])=[O:13])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

참가 물질

5

반응물 3

HCID 10403CyclooctanoneHCID 5049666Sodium triacetoxyborohydrideHCID 18611299HCID 18611299, 화합물

생성물 1

HCID 20794995HCID 20794995, 화합물수율 77%

시약·촉매·용매 1

HCID 21926011acetic acid N,N-dimethylformamide용매

실험 절차

To a stirred suspension of γ-tert-butyl-L-glutamic acid (4.06 g, 20.0 mmol) and cyclooctanone (3.15 g, 25 mmol) in N,N-dimethylformamide/acetic acid (99:1, v/v, 50 mL) was added sodium triacetoxyborohydride (6.36 g, 30.0 mmol) in small portions and the mixture was stirred overnight. After evaporation of the solvent, the residue was dissolved in water (50 mL). The pH was adjusted to 9 with 2 N sodium hydroxide solution, followed by extraction with diethylether (50 mL). Subsequently, the pH of the aqueous layer was carefully adjusted to 2.5 using 1.0 N hydrochloric acid. Extraction with dichloromethane afforded an organic layer, which was dried (magnesium sulphate) and concentrated under reduced pressure, yielding 4.82 g (77%) of the title compound as a white solid. ESI-MS: 314.2 (M+H)+, 336.2 (M+Na)+. Rf (silica gel; ethyl acetate/pyridine/acetic acid/water 63:20:6:11, v/v): 0.80.

후처리

  1. customAfter evaporation of the solvent
  2. dissolutionthe residue was dissolved in water (50 mL)
  3. extractionfollowed by extraction with diethylether (50 mL)
  4. extractionExtraction with dichloromethane
  5. customafforded an organic layer, which
  6. dry with materialwas dried (magnesium sulphate)
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e2a1594e01674934b1831cd8b4d0e173
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06903107B1

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