Hydrochloric Acid → HCID 86750394, compound

HRID 1452396Notes

Reaction equation

HRID 1452396 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]([NH:5][C@@H:6]1[C@H:12]([OH:13])[C@H:11]([CH3:14])[O:10][CH:8]([OH:9])[CH2:7]1)=[O:4].[CH3:17][S:18](Cl)(=[O:20])=[O:19].C(N(CC)CC)C.Cl>C(Cl)Cl>[F:16][C:2]([F:1])([F:15])[C:3]([NH:5][C@@H:6]1[C@:12]([S:18]([CH3:17])(=[O:20])=[O:19])([OH:13])[C@H:11]([CH3:14])[O:10][CH:8]([OH:9])[CH2:7]1)=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11042934HCID 11042934, compound

Product 1

HCID 86750394HCID 86750394, compoundYield 133.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1-t-butyl dimethylsilyloxy, 3-trifluoroacetamido-2,3,6-trideoxy-L-lyxohexopyranose (504 mg, 1.41 mmol) in CH2Cl2 (7 ml) at 0° C. were added methanesulfonyl chloride (218 μl, 2.82 mmol) and triethylamine (590 μl, 4.2 mmol). After 2 hours the reaction mixture was worked up with CH2Cl2 and HCl 0.1N. The organic layer was washed with a solution of NaHCO3 and brine then dried over MgSO4. The solvent was evaporated to give 1-t-butyl dimethyl silyloxy, 3-trifluoroacetamido-2,3,6 trideoxy-4 methanesulfonyl-L-lyxohexopyranose (604 mg, 98%).

Workup

  1. washThe organic layer was washed with a solution of NaHCO3 and brine
  2. dry with materialthen dried over MgSO4
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-296b8a8973534e3581655ad435376b6a
Source dataset
uspto-grants-1997_02
Patent number
US05606037

Reaction notes

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