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

HRID 413229Notes

Reaction equation

HRID 413229 reaction equation
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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-2b719e8a22314a7f990850f28486915f
Source dataset
uspto-grants-2003_05
Patent number
US06566373B2

Reaction notes

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