tert-Butyl isocyanate → HCID 22870585, compound

HRID 1938930Notes

Reaction equation

HRID 1938930 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, 0.23 mM) 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 C25 H42N2O3, 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-89362bf3719948a7aa331eef7cd15a3e
Source dataset
uspto-grants-1997_12
Patent number
US05693809

Reaction notes

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