Methanol → HCID 69010008, compound

HRID 42124Notes

Reaction equation

HRID 42124 reaction equation
[C:1]([C@@H:4]1[CH2:21][CH:20]2[C@:15]([CH3:23])([CH2:16][CH2:17][C:18](=[O:22])[CH2:19]2)[C@@H:14]2[C@@H:5]1[C@H:6]1[C@@:10]([CH2:12][CH2:13]2)([CH3:11])[C:9](=[O:24])[CH2:8][CH2:7]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[CH2:21][CH:20]2[C@:15]([CH3:23])([CH2:16][CH2:17][C:18](=[O:22])[CH2:19]2)[C@@H:14]2[C@@H:5]1[C@H:6]1[C@@:10]([CH2:12][CH2:13]2)([CH3:11])[C:9](=[O:24])[CH2:8][CH2:7]1)=[O:3]

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 690102647alpha-Carboxyandrostane-3,17-dione

Product 1

HCID 69010008HCID 69010008, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 7α-carboxyandrostane-3,17-dione (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-bc (500 mg, 70%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 3.63 (3H, s), 2.85 (1H, m), 2.50-0.75 (20H, m), 1.12 (3H, s), 0.86 (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-b11b897c0b3d4a9f8168cae229286614
Source dataset
uspto-grants-2013_09
Patent number
US08536160B2

Reaction notes

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