Water → HCID 69133340, compound

HRID 1912731Notes

Reaction equation

HRID 1912731 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH2:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1([C:17]([O:19][C@H:20]2[CH2:37][CH2:36][C@@:35]3([CH3:38])[CH:22]([C:23](=[O:40])[CH2:24][C@@H:25]4[C@@H:34]3[CH2:33][CH2:32][C@@:30]3([CH3:31])[C@H:26]4[CH2:27][CH2:28][C:29]3=[O:39])[CH2:21]2)=[O:18])C=CN=C1.O>C(Cl)Cl.CC(O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH:11][C:17]([O:19][C@H:20]1[CH2:37][CH2:36][C@@:35]2([CH3:38])[CH:22]([C:23](=[O:40])[CH2:24][C@@H:25]3[C@@H:34]2[CH2:33][CH2:32][C@@:30]2([CH3:31])[C@H:26]3[CH2:27][CH2:28][C:29]2=[O:39])[CH2:21]1)=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 187201N-BOC-ethylenediamineHCID 69810844HCID 69810844, compound

Product 1

HCID 69133340HCID 69133340, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

N-(tert-Butoxycarbonyl)ethylendiamine (0.20 mL) was added to a solution of 3β-(1-imidazolylcarbonyloxy)androstane-6,17-dione (200 mg) in CH2Cl2 (10 mL) and 2-propanol (1 mL). After heating under reflux for 9 hr, the mixture was cooled to room temperature and water was added. The organic layer was separated, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (SiO2; CH2Cl2:EtOAc 1:1) to give 3β-[N-(2-tert-butoxycarbonylaminoethyl)-carbamoyloxy]androstane-6,17-dione (184 mg, 76%). 1H-NMR (300 MHz, CDCl3, ppm from TMS): δ 5.02 (1H, bb), 4.84 (1H, bb), 4.56 (1H, m), 3.27 (4H, m), 2.50-1.20 (20H, m), 1.45 (9H, s), 0.87 (3H, s), 0.80 (3H, s).

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 9 hr
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customThe residue was purified by flash chromatography (SiO2; CH2Cl2:EtOAc 1:1)

Sources & evidence

ORD record
ord-bb7856f50c81444a8a48761852b190ca
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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