Hydrochloric Acid → HCID 54321503, compound

HRID 1287576Notes

Reaction equation

HRID 1287576 reaction equation
C(O[CH:5]1[O:26][C@H:25]([CH2:27][O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@H:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:15]([NH:36][C:37](=[O:39])[CH3:38])[C@H:6]1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)C.Cl.C([Cl:44])(=O)C>O1CCOCC1>[C:37]([NH:36][C@H:15]1[C@@H:16]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C@@H:25]([CH2:27][O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:26][C@H:5]([Cl:44])[C@@H:6]1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:39])[CH3:38]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 54333303HCID 54333303, compound

Product 1

HCID 54321503HCID 54321503, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Dissolve 1.5 g. of 3-acetamido-3-deoxy-2,4,6-tri-O-benzyl-D-galactopyranosyl acetate in 75 ml. of dioxane containing 4% by weight of hydrogen chloride and add 35 ml. of acetyl chloride to the solution. Allow the mixture to stand in a dry nitrogen atmosphere for 16 hours at 40°. Evaporate the mixture to dryness in vacuo to a syrup. Repeatedly co-distil this residue with dry toluene until all hydrogen chloride is removed. Crystallize the resultant residue with hexane to obtain the title product of this example. Yield 1.1 g., m.p. 158°-159° (decomp.), [α]D26 + 169.9°.

Workup

  1. dissolutionDissolve 1.5 g
  2. customEvaporate the mixture to dryness in vacuo to a syrup
  3. customRepeatedly co-distil this residue with dry toluene until all hydrogen chloride is removed
  4. customCrystallize the resultant residue with hexane

Sources & evidence

ORD record
ord-8f1a77578f6c4ef281bb70e04aa43886
Source dataset
uspto-grants-1976_10
Patent number
US03985727

Reaction notes

Loading…