Hydrochloric Acid → HCID 86737779, compound

HRID 1680245Notes

Reaction equation

HRID 1680245 reaction equation
[CH3:1][C:2]1[C:3](=[O:23])[CH2:4][C@@:5]23[CH2:18][CH2:17][N:16](C)[C@@H:13]([C@@H:14]2[CH:15]=1)[CH2:12][C:11]1[CH:10]=[CH:9][C:8]([O:20][CH3:21])=[C:7]([OH:22])[C:6]3=1.Cl.[H][H]>C(O)C.[Pd]>[OH:22][C:7]1[C:6]2[C@:5]34[CH2:18][CH2:17][NH:16][C@@H:13]([C@@H:14]3[CH2:15][C@H:2]([CH3:1])[C:3](=[O:23])[CH2:4]4)[CH2:12][C:11]=2[CH:10]=[CH:9][C:8]=1[O:20][CH3:21]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 57237521HCID 57237521, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86737779HCID 86737779, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 14 (22.0 g, 70 mmole) in 95% ethanol (200 ml) was added concentrated HCl (12 ml) and 10% palladium on activated carbon (2.0 g). The mixture was hydrogenated at an initial pressure of 50 psi until the uptake of hydrogen ceased. The mixture was filtered from the catalyst and the filtrate evaporated to a small volume. The residue was dissolved in water, the solution made basic with concentrated NH4OH and extracted with three portions of chloroform. The chloroform extracts were washed with dilute NH4OH, dried and evaporated to a thick syrup which crystallized on the addition of ethyl acetate. The crystals were collected and dried to give 14.4 g (65%) of 16a as white needles, mp 163°-165°. Recrystallization from acetone gave analytically pure 16a as the hemi-acetone solvate, 166°-167° NMR: δ 6.55, s, 2H (aromatic); 6.40, broad, 1H (hydroxyl H); 4.22, d, 1H (H-5α, J=13 Hz); 3.77 (CH3O--); 2.38 (CH3N); 0.87, d, 3H (7α-CH3, J=6.5 Hz).

Workup

  1. filtrationThe mixture was filtered from the catalyst
  2. customthe filtrate evaporated to a small volume
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with three portions of chloroform
  5. washThe chloroform extracts were washed with dilute NH4OH
  6. customdried
  7. customevaporated to a thick syrup which
  8. customcrystallized on the addition of ethyl acetate
  9. customThe crystals were collected
  10. customdried

Sources & evidence

ORD record
ord-0b3c64b4c3424e658e22170846b8ca53
Source dataset
uspto-grants-1981_06
Patent number
US04272541

Reaction notes

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