Hydrazine → HCID 178516766, compound

HRID 46213Notes

Reaction equation

HRID 46213 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@@H:12]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@H:11]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@@H:10]([CH2:38][O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[O:9]2)=[CH:4][C:3]=1[CH2:47][C:48]([NH:50][CH2:51][C:52]([O:54]C)=O)=O.[NH2:56][NH2:57]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@@H:12]([O:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C@H:11]([O:30][CH2:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C@@H:10]([CH2:38][O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[O:9]2)=[CH:4][C:3]=1[CH2:47][C:48]1[NH:50][CH2:51][C:52](=[O:54])[NH:57][N:56]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 67288462HCID 67288462, compound2×

Product 1

HCID 178516766HCID 178516766, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 2-(2-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)acetamido)acetate (compound 54, 1.1 g, 1.44 mmol) in MeOH (20 ml) was added hydrazine anhydrous (2 ml) at room temperature. Then, the reaction temperature was raised to 60° C., and maintained for overnight. After reaction complete, the solution was evaporated in vacuo, and the residue was dissolved in acetic acid (10 ml) with ammonium acetate (1 g). The reaction solution was refluxed for 1 day. The resulting solution was cooled to room temperature, and then evaporated under reduced pressure. The residue was purified with column chromatography (Hx/EtOAc=1/1) to afford to title compound (826 mg, 77% overall yield) as white solid.

Workup

  1. temperaturemaintained for overnight
  2. customAfter reaction complete
  3. customthe solution was evaporated in vacuo
  4. dissolutionthe residue was dissolved in acetic acid (10 ml) with ammonium acetate (1 g)
  5. temperatureThe reaction solution was refluxed for 1 day
  6. temperatureThe resulting solution was cooled to room temperature
  7. customevaporated under reduced pressure
  8. customThe residue was purified with column chromatography (Hx/EtOAc=1/1)

Sources & evidence

ORD record
ord-c09b57ecb6f04c94b4bf3ac0aaa9a527
Source dataset
uspto-grants-2013_09
Patent number
US08541380B2

Reaction notes

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