Tetrahydrofuran → HCID 67744901, compound

HRID 1648440Notes

Reaction equation

HRID 1648440 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 -CH2), 4.07 (1 H, dd, 1/2 C21 -CH2). 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-27660e42c3a14ed59d53680dee6475d2
Source dataset
uspto-grants-1995_07
Patent number
US05436237

Reaction notes

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