Hydrochloric Acid → HCID 22867510, compound

HRID 1901948Notes

Reaction equation

HRID 1901948 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.Cl.[C:14]1([CH2:20][C@H:21]([N:37]=[N+:38]=[N-:39])[C@@H:22]([OH:36])[C@H:23]([OH:35])[C@@H:24]([N:32]=[N+:33]=[N-:34])[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl.C(OCC)C>[C:14]1([CH2:20][C@H:21]([N:37]=[N+:38]=[N-:39])[C@@H:22]([O:36][S:2]([CH3:1])(=[O:4])=[O:3])[C@H:23]([OH:35])[C@@H:24]([N:32]=[N+:33]=[N-:34])[CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 15012933HCID 15012933, compound

Product 1

HCID 22867510HCID 22867510, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 13.5 μL (0.170 mmol) of methanesulfonyl chloride in 300 μL of methylene chloride was slowly added to a cold (0° C.) solution of 80 mg (0.23 mmol) of the subtitled intermediate of Preparation 1D and 32 μL (0.23 mmol) of triethylamine in 0.6 mL of methylene chloride. The reaction mixture was warmed to room temperature, allowed-to react for 15 minutes and then poured into 50 mL of a 3:2 mixture of diethyl ether and 0.1N hydrochloric acid. The resulting layers were separated and the organic layer was washed with a half-saturated sodium bicarbonate solution and then reduced to dryness under reduced pressure to provide a foam. This foam was purified using column chromatography (eluted with a 1:2 ethyl acetate/methylene chloride solution). The fractions containing the desired product were combined and reduced to dryness under reduced pressure to provide 100 mg of a 60:40 mixture of the desired subtitled intermediate and the starting material, 1,6-diphenyl-2(S),5(S)-diazido-3(R),4(R)-dihydroxyhexane.

Workup

  1. customallowed-to react for 15 minutes
  2. customThe resulting layers were separated
  3. washthe organic layer was washed with a half-saturated sodium bicarbonate solution
  4. customto provide a foam
  5. customThis foam was purified
  6. washeluted with a 1:2 ethyl acetate/methylene chloride solution)
  7. additionThe fractions containing the desired product
  8. customto provide

Sources & evidence

ORD record
ord-b946c8c0832f43cea2f570f00a35c6cd
Source dataset
uspto-grants-1996_11
Patent number
US05578608

Reaction notes

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