Sodium Bromide → Benzyl (4-oxotetrahydrofuran-3-yl)carbamate

HRID 413229노트

반응식

HRID 413229 반응식
C(=O)(O)[O-].[Na+].[OH:6][CH:7]1[CH:11]([NH:12][C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:10][O:9][CH2:8]1.[Br-].[Na+].CC1(C)N([O])C(C)(C)CCC1>CCOC(C)=O.C1(C)C=CC=CC=1.O>[CH2:16]([O:15][C:13]([NH:12][CH:11]1[CH2:10][O:9][CH2:8][C:7]1=[O:6])=[O:14])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

참가 물질

8

반응물 4

HCID 253881Sodium BromideHCID 516892Sodium BicarbonateHCID 2724126TempoHCID 18523488Benzyl (3S,4S)-4-hydroxytetrahydrofuran-3-ylcarbamate

생성물 1

HCID 18523485Benzyl (4-oxotetrahydrofuran-3-yl)carbamate

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of bleach (100 ml), containing sodium bicarbonate (7.34 g), was added dropwise to a rapidly stirred mixture of 3-hydroxy-4-benzyloxycarbonylamino-tetrahydrofuran (21 g, 88 mmol), sodium bromide (9.4 g), TEMPO (50 mg) in EtOAc (140 ml), toluene (140 ml) and water (40 ml). After a persistant orange colour developed the mixture was extracted with EtOAc and the combined organic layers were washed with saturated sodium bicarbonate, brine and dried (MgSO4). Evaporation under reduced pressure and purification of the residue by column chromatography afforded the title compound as white crystals, 18 g, 87%.

후처리

  1. extractionwas extracted with EtOAc
  2. washthe combined organic layers were washed with saturated sodium bicarbonate, brine
  3. dry with materialdried (MgSO4)
  4. customEvaporation
  5. customunder reduced pressure and purification of the residue by column chromatography

출처 및 근거

ORD 기록
ord-2b719e8a22314a7f990850f28486915f
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06566373B2

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