tert-Butyl isocyanate → HCID 22881410, compound

HRID 726865Notes

Reaction equation

HRID 726865 reaction equation
[CH3:1][N:2]1[C:19](=[O:20])[CH2:18][CH2:17][C@@:16]2([CH3:21])[CH:3]1[CH2:4][C@H:5]([CH3:23])[C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C@@H:10]2[OH:22].C1CCN2C(=NCCC2)CC1.[C:35]([N:39]=[C:40]=[O:41])([CH3:38])([CH3:37])[CH3:36]>C(Cl)Cl.C(OCC)(=O)C>[C:35]([NH:39][C:40]([O:22][C@H:10]1[CH2:9][CH2:8][C@H:7]2[C@H:6]3[C@H:15]([CH2:14][CH2:13][C@:11]12[CH3:12])[C@:16]1([CH3:21])[C@H:3]([N:2]([CH3:1])[C:19](=[O:20])[CH2:18][CH2:17]1)[CH2:4][CH:5]3[CH3:23])=[O:41])([CH3:38])([CH3:37])[CH3:36]

Participants

6

Reactant 3

HCID 62412tert-Butyl isocyanateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22861808HCID 22861808, compound

Product 1

HCID 22881410HCID 22881410, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 70, 51 mg in 4 ml methylene chloride was added DBU (200 microliters) followed by 63.65 mg. t-butylisocyanate. After stirring the mixture for 48 hours at room temperature, the reaction mixture was diluted with ethyl acetate, the organic layer washed with water, brine, dried and concentrated to a residue which was purified by preparative chromatography over silica gel using 3:1 CHCl3 /acetone to yield pure title compound 72.

Workup

  1. washthe organic layer washed with water, brine
  2. customdried
  3. concentrationconcentrated to a residue which
  4. customwas purified by preparative chromatography over silica gel using 3:1 CHCl3 /acetone

Sources & evidence

ORD record
ord-53e2e8cccfd442e8a44cab9b0b44c1db
Source dataset
uspto-grants-1998_01
Patent number
US05710275

Reaction notes

Loading…