Water → HCID 67744913, compound

HRID 2082412Notes

Reaction equation

HRID 2082412 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].O1[C:7]23[C@:23]([CH3:28])([CH2:24][CH2:25][C:26](=[O:27])[CH:6]12)[C@@H:22]1[C@H:10]([C@H:11]2[C@:19]([CH3:29])([CH2:20][CH2:21]1)[C@@H:14]([C@H:15]([CH3:18])[CH2:16][OH:17])[CH2:13][CH2:12]2)[CH2:9][CH2:8]3.[N-:30]=[N+]=[N-].[Na+].S(=O)(=O)(O)O.O>CS(C)=O>[C:1]([OH:4])(=[O:3])[CH3:2].[NH2:30][C:6]1[C:26](=[O:27])[CH2:25][CH2:24][C@@:23]2([CH3:28])[C:7]=1[CH:8]=[CH:9][C@@H:10]1[C@@H:22]2[CH2:21][CH2:20][C@@:19]2([CH3:29])[C@H:11]1[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:18])[CH2:16][OH:17]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 33557Sodium AzideHCID 86745917HCID 86745917, compound

Product 1

HCID 67744913HCID 67744913, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a vigorously stirred solution of the (20S)-4,5-epoxy-21-hydroxy-20-methylpregnan-3-one acetate (2.0 g, 5.15 mmole) obtained in Example 7, in dimethyl sulfoxide (70 mL) and heated to 60° C., there was added sodium azide (5.4 g) and then concentrated sulfuric acid (0.37 mL). The mixture was quickly brought to a temperature of 100° C. and held at that temperature for 1 hour. The cooled mixture was then poured into cold water (450 mL). The solids were collected by filtration, washed with water, and dried by suction to give a yellow solid which was purified by flash chromatography to give (20S)-4-amino-21-hydroxy-20-methylpregna-4,6-dien-3-one acetate (1.04 g, 52.5%). IR 3488, 3446, 3360, 1740, 1668, 1612 (m), 1592 (m), 1562 (m), 1252 cm-1 ; MS (CI) 386 (20%, M +1), 326 (100%, M+1 - AcOH); 1H NMR (CDCl3)δ0.78 (3H, s, C18 -Me), 1.03 (d, C22 -Me), 1.06 (s, C19 -Me), 2.07 (S, Ac-Me), 3.69+3.78 (3H, v br+dd, NH2 +1/2C21 -CH2), 4.09 (1H, dd, 1/2C21 -CH2), 5.97 (1H, dd), 6.30 (1H, dd). This compound has the following structure: ##STR5##

Workup

  1. customwas quickly brought to a temperature of 100° C.
  2. filtrationThe solids were collected by filtration
  3. washwashed with water
  4. customdried by suction
  5. customto give a yellow solid which
  6. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-4080c9eaefcf47e496e83410346d48ef
Source dataset
uspto-grants-1993_02
Patent number
US05189032

Reaction notes

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