Methanol → HCID 69009208, compound

HRID 42091Notes

Reaction equation

HRID 42091 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)([OH:3])=[O:2].CO.[CH3:27]CN=C=NCCCN(C)C.O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:27][O:2][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:3]

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69014555HCID 69014555, compound

Product 1

HCID 69009208HCID 69009208, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 6α-carboxyandrostane-3,17-dione (Prepn. 16, 680 mg) in CH2Cl2 (30 mL) at 0° C., MeOH (160 μL), DMAP (20 mg) and EDAC (800 mg) were added. After stirring overnight at room temperature, H2O was added and the mixture was extracted with CH2Cl2 (2×). The combined organic extracts were washed with H2O, brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by flash chromatography (SiO2, n-hexane/EtOAc 60/40) to give the title compound II-ag (500 mg, 70%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 3.59 (3H, s), 2.53-0.75 (21H, m), 1.02 (3H, s), 0.79 (3H, s).

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (2×)
  2. washThe combined organic extracts were washed with H2O, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by flash chromatography (SiO2, n-hexane/EtOAc 60/40)

Sources & evidence

ORD record
ord-04d4f36299c147a0ba6723e5763ed264
Source dataset
uspto-grants-2013_09
Patent number
US08536160B2

Reaction notes

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