Hydrochloric Acid → HCID 86734704, compound

HRID 866337Notes

Reaction equation

HRID 866337 reaction equation
[CH3:1][C@H:2]([OH:10])[C@@H:3]([OH:9])[C@@H:4]([NH2:8])[CH2:5][CH:6]=[O:7].FC(F)(F)C([O:15][C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])=O.[ClH:24]>C(OCC)C>[Cl:24][C@:6]1([O:10][C@@H:2]([CH3:1])[C@@:3]([O:15][C:16](=[O:21])[C:17]([F:18])([F:19])[F:20])([OH:9])[C@@H:4]([NH:8][C:16](=[O:15])[C:17]([F:20])([F:19])[F:18])[CH2:5]1)[OH:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9845Trifluoroacetic anhydrideHCID 1601283-Amino-2,3,6-trideoxy-L-lyxo-hexose

Product 1

HCID 86734704HCID 86734704, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

One gram of daunosamine (II) hydrochloride was suspended in anhydrous diethyl ether and treated at 0° C. with 8 ml. of trifluoroacetic anhydride. After allowing the suspension to stand for two hours at 0° C. and one hour at room temperature, the solvent was removed under reduced pressure and the residue was crystallized from dichloromethane to yield 1.1 g. of 2,3,6-trideoxy-1-trifluoroacetoxy-3-trifluoroacetamido-4-trifluoroacetoxy-L-lyxopyranose (IIA), having a m.p. of 132°-134° C. and a mass spectrum m/e 391 (M-44), 322 (M-113). 0.5 g of (IIA) in anhydrous diethyl ether was treated at 0° C. with anhydrous gaseous hydrogen chloride. After standing at +5° C. overnight, the solvent was removed in vacuo to yield 1-chloro-2,3,6-trideoxy-3-trifluoroacetamido-4-trifluoroacetoxy-α-L-lyxohexopyranose (IIB) as crystalline product. The NMR spectrum of (IIB) in CDCl3 was as follows:

Workup

  1. additiontreated at 0° C. with 8 ml
  2. customthe solvent was removed under reduced pressure
  3. customthe residue was crystallized from dichloromethane
  4. customto yield 1.1 g
  5. waitAfter standing at +5° C. overnight
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-65073ca80bd44274a9ea7d38df0aa284
Source dataset
uspto-grants-1978_07
Patent number
US04098798

Reaction notes

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