Benzyl isocyanate → HCID 22870605, compound

HRID 1938931Notes

Reaction equation

HRID 1938931 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C@H:11]([N:12]([CH3:22])[C:13](=[O:21])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.[CH2:23]([N:30]=[C:31]=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>N1C=CC=CC=1>[CH2:23]([NH:30][C:31]([O:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C@H:11]([N:12]([CH3:22])[C:13](=[O:21])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 10171822HCID 10171822, compound

Product 1

HCID 22870605HCID 22870605, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 17β-hydroxy-4-methyl-5α-4-azaandrostan-3-one (61 mg) in pyridine (0.60 ml) was added benzyl isocyanate (54 mg, 0.40 mmol). The mixture was stirred at 60°-70° C. under N2 for 18 hr and pumped in vacuo to remove pyridine. The residue was purified using a silica gel plate (2000 m) developed with ethyl acetate (Rf=0.37, run in EtOAc) to give the title compound; m.p. is 216°-217° C.

Workup

  1. customto remove pyridine
  2. customThe residue was purified

Sources & evidence

ORD record
ord-ce786489f7694c9f8b718111d8b1856e
Source dataset
uspto-grants-1997_12
Patent number
US05693809

Reaction notes

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