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

HRID 413229ノート

反応式

HRID 413229 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-2b719e8a22314a7f990850f28486915f
出典データセット
uspto-grants-2003_05
特許番号
US06566373B2

反応ノート

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