Acetic Acid → HCID 86660594, compound

HRID 2367947Notes

Reaction equation

[C:1]([C@@:9]([CH2:41][OH:42])([OH:40])[C@:10]([C:32](=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([OH:31])[C@:11]([C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([OH:22])[C:12](C(=O)C1C=CC=CC=1)=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BrH:43].CC(O)=O>ClCCl>[Br:43][C:12]([C@:11]([C:23](=[O:30])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([C@:10]([C:32](=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C@:9]([C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH2:41][OH:42])[OH:40])[OH:31])[OH:22])=[O:13]

Participants

Conditions

Temperature: 0 °C

Procedure

Crude tetra-benzoyl-L-ribose 20 (17.0 g, 30.0 mmol) was dissolved in dichloromethane (150 mL) under an atmosphere of argon at 0° C. To this solution was added 33% HBr in AcOH (32.6 mL, 180.0 mmol of HBr) and the reaction was stirred for 30 min at 0° C. then brought to room temperature for 30 min. Dichloromethane (150 mL) was added and the reaction mixture was washed with 125 mL of cold water, dilute NaHCO3, two times with saturated NaHCO3 and brine then dried over Na2SO4 and concentrated in vacuo to give 21 as a off-white solid (13.3 g, 25.3 mmol, 84%). This material was used without further purification.

Workup

waitthen brought to room temperature for 30 min
washthe reaction mixture was washed with 125 mL of cold water, dilute NaHCO3, two times with saturated NaHCO3 and brine
dry with materialthen dried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-aa430c0da2674bb6b141ae7796147362
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703723B2

Reaction notes

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