Hydrochloric Acid → HCID 67270563, compound

HRID 1695543Notes

Reaction equation

HRID 1695543 reaction equation
[OH:1][C@@H:2]1[C@H:15]2[C@@H:6]([CH2:7][CH2:8][C:9]3[C@:14]2([CH3:16])[CH2:13][CH:12]([CH:17]=O)[C:11](=O)[CH:10]=3)[C@@H:5]2[CH2:20][CH2:21][C@:22]3([C:26]4([CH2:30][O:29][CH2:28][O:27]4)[O:25][CH2:24][O:23]3)[C@@:4]2([CH3:31])[CH2:3]1.[NH:32]([C:34]1[CH:35]=[C:36]([CH:40]=[CH:41][CH:42]=1)[C:37]([OH:39])=[O:38])[NH2:33].C([O-])(=O)C.[K+].Cl>C(O)C.O>[OH:1][C@H:2]1[C@@H:15]2[C@H:6]([CH2:7][CH2:8][C:9]3[C@@:14]2([CH3:16])[CH2:13][C:12]2[CH:17]=[N:33][N:32]([C:34]4[CH:35]=[C:36]([CH:40]=[CH:41][CH:42]=4)[C:37]([OH:39])=[O:38])[C:11]=2[CH:10]=3)[C@H:5]2[CH2:20][CH2:21][C@@:22]3([C:26]4([CH2:30][O:29][CH2:28][O:27]4)[O:25][CH2:24][O:23]3)[C@:4]2([CH3:31])[CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 517044Potassium AcetateHCID 27365213-Hydrazinobenzoic acidHCID 59810282HCID 59810282, compound

Product 1

HCID 67270563HCID 67270563, compoundYield 106.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

(8S,9S,10R,11S,13S,14S,17R)-11-hydroxy-10,13-dimethyl-3-oxo-1,2,3,6,7,8,9,10,11,12,13,14,15,16-tetradecahydrodispiro[cyclopenta[a]phenanthrene-17,4′-[1,3]dioxolane-5′,4″-[1,3]dioxolane]-2-carbaldehyde (Steroids 2003, (68), 177-191) (1.4 g, 3.24 mmol) was dissolved in ethanol (10 ml) and water (1 ml). 3-hydrazinobenzoic acid (0.493 g, 3.24 mmol) and potassium acetate (0.491 g, 5 mmol) were added to give a brown solution which was stirred for 1 hour at room temperature. The mixture was poured into a separation funnel containing 1M HCl (200 ml) and was extracted with DCM (3 times 150 ml). The combined organic phases were washed with water (2 times 100 ml) and 1M NaOH. The organic phase was washed with brine, dried over Na2SO4, filtered and the solvent was evaporated to give 1.9 g of a brownish foam. The crude product was purified on a silica gel column (Heptane:EtOAc=1:1) and the product containing fractions were evaporated under reduced pressure to yield 1.5 g of the desired compound. APCI-MS m/z: 549 [MH+].

Workup

  1. customto give a brown solution which
  2. additionThe mixture was poured into a separation funnel
  3. extractionwas extracted with DCM (3 times 150 ml)
  4. washThe combined organic phases were washed with water (2 times 100 ml) and 1M NaOH
  5. washThe organic phase was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6493fd6cf970400e94d784ec9fc9b167
Source dataset
uspto-grants-2012_04
Patent number
US08163724B2

Reaction notes

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