Hydrochloric Acid → HCID 15406636, compound

HRID 1415880Notes

Reaction equation

HRID 1415880 reaction equation
B#B.[CH2:3]([C@@:7]1([CH2:28][CH3:29])[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]2[CH:20]=[C:21]([O:26][CH3:27])[C:22]([O:24][CH3:25])=[CH:23][C:10]=2[S:9][CH2:8]1)[CH2:4][CH2:5][CH3:6].Cl>C1COCC1>[CH2:3]([C@@:7]1([CH2:28][CH3:29])[NH:13][C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]2[CH:20]=[C:21]([O:26][CH3:27])[C:22]([O:24][CH3:25])=[CH:23][C:10]=2[S:9][CH2:8]1)[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6328200DiboronHCID 15406635HCID 15406635, compound

Product 1

HCID 15406636HCID 15406636, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1M solution of diborane in THF (200 ml) was added to a solution of the product (64.0 g) from step (m) in THF (350 ml). The reaction mixture was stirred at room temperature for a period of 17 hours, then 6N HCl (150 ml) was added and the solution was concentrated in vacuo to remove THF. The aqueous residue was basified with 50% NaOH and extracted with EtOAc. The EtOAc layer was separated, dried and concentrated in vacuo to afford an oil which was chromatographed on silica gel, using hexane: EtOAc (85:15) as eluant, to give the title product (25.5 g) as a beige solid, mp 64-66° C. 1H NMR consistent for proposed structure.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. customto remove THF
  3. extractionextracted with EtOAc
  4. customThe EtOAc layer was separated
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customto afford an oil which
  8. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-4cd3aca17a9546d285222e276d0e4b15
Source dataset
uspto-grants-1999_06
Patent number
US05910494

Reaction notes

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