Ammonia → HCID 69008521, compound

HRID 1912684Notes

Reaction equation

HRID 1912684 reaction equation
[C:1]([C@@H:4]1[CH:21]2[C@:16]([CH3:23])([CH2:17][CH2:18][C:19](=[O:22])[CH2:20]2)[C@@H:15]2[C@H:6]([C@H:7]3[C@@:11]([CH2:13][CH2:14]2)([CH3:12])[C:10](=[O:24])[CH2:9][CH2:8]3)[CH2:5]1)(O)=[O:2].[NH3:25]>C1(C)C=CC=CC=1.O=S(Cl)Cl.CO>[C:1]([C@@H:4]1[CH:21]2[C@:16]([CH3:23])([CH2:17][CH2:18][C:19](=[O:22])[CH2:20]2)[C@@H:15]2[C@H:6]([C@H:7]3[C@@:11]([CH2:13][CH2:14]2)([CH3:12])[C:10](=[O:24])[CH2:9][CH2:8]3)[CH2:5]1)(=[O:2])[NH2:25]

Participants

6

Reactant 2

HCID 222AmmoniaHCID 69014555HCID 69014555, compound

Product 1

HCID 69008521HCID 69008521, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred suspension of 6α-carboxyandrostane-3,17-dione (II-aq, Prepn. 17, 600 mg) in dry toluene (12 mL), SOCl2 (623 μL) was added. After stirring 5.5 h at 85° C. the solution was cooled at 0° C. and 2M NH3 solution in MeOH (2.97 mL) was added. After stirring overnight at room temperature, the mixture was evaporated to dryness. The residue was treated with CH2Cl2 and H2O and extracted with CH2Cl2. The combined organic extracts were washed with 10% K2CO3 solution, brine, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (SiO2, n-hexane/acetone 50/50) to give the title compound II-ar (90 mg, 15%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 7.27 (bs, 1H), 6.78 (bs, 1H), 2.50-0.72 (m, 21H), 1.00 (s, 3H), 0.80 (s, 3H).

Workup

  1. additionwas added
  2. temperaturewas cooled at 0° C.
  3. stirringAfter stirring overnight at room temperature
  4. customthe mixture was evaporated to dryness
  5. additionThe residue was treated with CH2Cl2 and H2O
  6. extractionextracted with CH2Cl2
  7. washThe combined organic extracts were washed with 10% K2CO3 solution, brine
  8. dry with materialdried over Na2SO4
  9. customevaporated to dryness
  10. customThe residue was purified by flash chromatography (SiO2, n-hexane/acetone 50/50)

Sources & evidence

ORD record
ord-336d3e0b48b84b299490e5734b1bcd61
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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