Hexane → HCID 54112621, compound

HRID 1508613Notes

Reaction equation

HRID 1508613 reaction equation
B(Br)(Br)Br.ClCCl.C([O:15][C@@H:16]1[C@@H:20]([CH2:21][O:22]CC2C=CC=CC=2)[S:19][CH:18]([N:30]2[CH:37]=[CH:36][C:34]([NH2:35])=[N:33][C:31]2=[O:32])[C@H:17]1[F:38])C1C=CC=CC=1.CCCCCC>ClCCl>[F:38][C@H:17]1[C@H:16]([OH:15])[C@@H:20]([CH2:21][OH:22])[S:19][CH:18]1[N:30]1[CH:37]=[CH:36][C:34]([NH2:35])=[N:33][C:31]1=[O:32]

Participants

5

Reactant 3

HCID 8058HexaneHCID 22277759Boron tribromide dichloromethaneHCID 118109055HCID 118109055, compound

Product 1

HCID 54112621HCID 54112621, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.065 mL of a 1 mol/L boron tribromide-dichloromethane solution was added to a solution of 9.6 mg of 1-(3,5-bis-O-benzyl-2-deoxy-2-fluoro-4-thio-D-arabinofuranosyl)cytosine in 1 mL of dichloromethane under cooling on ice. While the temperature was gradually increased to room temperature, the obtained mixture was stirred for 2 hours. Thereafter, hexane was added to the reaction mixture, and a solid was then collected by filtration. The obtained solid was washed with toluene and ethyl acetate, so as to obtain 5.3 mg of 1-(2-deoxy-2-fluoro-4-thio-D-arabinofuranosyl)cytosine in the form of a white solid.

Workup

  1. temperatureunder cooling on ice
  2. filtrationa solid was then collected by filtration
  3. washThe obtained solid was washed with toluene and ethyl acetate

Sources & evidence

ORD record
ord-ac02bb4f20b84aa2a5473e888aa3d37d
Source dataset
uspto-grants-2015_12
Patent number
US09221865B2

Reaction notes

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