tert-Butyl isocyanate → HCID 22870585, compound

HRID 975848Notes

Reaction equation

HRID 975848 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([CH2:20][CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[C@H:12]([N:13]([CH3:23])[C:14](=[O:22])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3.[C:24]([N:28]=[C:29]=[O:30])([CH3:27])([CH3:26])[CH3:25].N12CCCN=C1CCCCC2>C1C=CC=CC=1>[C:24]([NH:28][C:29]([O:1][CH2:2][CH:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([CH2:20][CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[C@H:12]([N:13]([CH3:23])[C:14](=[O:22])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)=[O:30])([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 62412tert-Butyl isocyanateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22862543HCID 22862543, compound

Product 1

HCID 22870585HCID 22870585, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred solution of 17-(hydroxymethyl)-4-methyl-5α-4-azaandrostan-3-one (0.048 g, 0.15 mM) in dried benzene (5 mL) was added at room temperature t-butylisocyanate (0.03 mL, 0.23mM) followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (0.023 mL, 0.15 mM). After stirring for two days, the volatiles were removed in vacuo and the residue flash chromatographed on silica gel using ethyl acetate as eluant to give the title compound as a white solid. MS M+1 calculated for C25H42N2O3, mw=418.55; observed m/e 419.

Workup

  1. customthe volatiles were removed in vacuo
  2. customthe residue flash chromatographed on silica gel

Sources & evidence

ORD record
ord-9d0eb94819334e77b33b633f1fc01de9
Source dataset
uspto-grants-1997_03
Patent number
US05610162

Reaction notes

Loading…