Tetrahydrofuran → HCID 67744901, compound

HRID 893038Notes

Reaction equation

HRID 893038 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[N:5]([C:8]1[C:28](=[O:29])[CH2:27][CH2:26][C@@:25]2([CH3:30])[C:9]=1[CH2:10][CH2:11][C@@H:12]1[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:31])[C@H:13]1[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH3:20])[CH2:18][OH:19])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1>O>[C:1]([OH:4])(=[O:3])[CH3:2].[NH2:5][C:8]1[C:28](=[O:29])[CH2:27][CH2:26][C@@:25]2([CH3:30])[C:9]=1[CH2:10][CH2:11][C@@H:12]1[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:31])[C@H:13]1[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH3:20])[CH2:18][OH:19]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 86745919HCID 86745919, compound

Product 1

HCID 67744901HCID 67744901, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of (20S)-4-azido-21-hydroxy-20-methylpregn-4-en-3-one acetate (1.4 g, 3.39 mmole), triphenylphosphine (1.08 g), tetrahydrofuran (25 mL) and water (7 mL) was heated at reflux temperature under argon for 18 hours. The solvents were removed from the cooled reaction and the residue was purified by flash chromatography to give (20S)-4-amino-21-hydroxy-20-methylpregn-4-en-3-one acetate (1.1 g, 84%). IR 3470, 3366, 1732, 1674, 1618, 1584, 1254 cm-1 ; MS (CI) 388 (100%, M+1), 328 (70% M+1-AcOH); 1H NMR (CDCl3) δ 0.72 (3H, s, C18 -Me), 1.00 (d, C22 -Me), 1.14 (s, C19 -Me), 2.04 (s, Ac-Me), 3.43 (2H, v br, NH2), 3.76 (1H, dd, 1/2 C21 -CH1), 4.07 (1H, dd, 1/2 C21 -CH1). This compound has the following structure: ##STR8##

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature under argon for 18 hours
  3. customThe solvents were removed from the cooled reaction
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-ec2889fdf6d942af897fa8ba0ef68e26
Source dataset
uspto-grants-1992_06
Patent number
US05120840

Reaction notes

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