HCID 14980114, compound → HCID 69208040, compound

HRID 2222130Notes

Reaction equation

HRID 2222130 reaction equation
[NH2:1][C:2]1[C:19]([O:20][CH3:21])=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[CH2:22])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1.[CH3:23]C(C)(C)C(C(OC(C(=O)C(C)(C)C)=O)=O)=O>C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:19]([O:20][CH2:21][CH3:23])=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[CH2:22])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 14980114HCID 14980114, compoundHCID 46882565HCID 46882565, compound

Product 1

HCID 69208040HCID 69208040, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Representative preparation of 3-formamide estrane derivatives: Preparation of 3-formamide-17-methylene-2-methoxyestra-1,3,5(10)-triene (Compound #88): 3-Amino-17-methylene-2-methoxyestra-1,3,5(10)-triene (293 mg, 0.99 mmol) was dissolved in chloroform (1 mL) and trimethylacetyl formic anhydride (170 mg, 1.30 mmol, prepared as in Vlietstra et al Recueil, 1982, 101, 460) was added. The mixture was stirred 40 min, after which, the solvent was removed under reduced pressure. The product was purified by titurating with hexanes and isolating the precipitate by decanting after the precipitate was centrifuged. Obtain 150 mg white powder (0.417 mmol, 42% yield). 1H NMR (300 MHz, CD3OD) δ 8.27 (s, 1H), 7.88 (s, 1H), 6.94 (s, 1H), 4.72-4.67 (m, 2H), 3.88 (s, rotamer 1) and 3.86 (s, rotamer 2, total 3H), 2.87-2.76 (m, 2H), 2.66-1.19 (m, 13H), 0.87 (s, 3H).

Workup

  1. customafter which, the solvent was removed under reduced pressure
  2. customThe product was purified
  3. customisolating the precipitate
  4. customby decanting after the precipitate

Sources & evidence

ORD record
ord-fca8ac55cc8346178dfabf4082c428ad
Source dataset
uspto-grants-2008_05
Patent number
US07371741B2

Reaction notes

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