3,4-Dichlorophenyl isocyanate → HCID 58219407, compound

HRID 1261841Notes

Reaction equation

HRID 1261841 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[OH:12][C@@H:13]1[CH2:20][N:19]([CH2:21][CH2:22][CH2:23][C@@H:24]2[N:28]3[C:29](=[O:34])[C@H:30]([CH3:33])[NH:31][CH2:32][C:27]3([CH3:35])[O:26][CH2:25]2)[CH2:18][CH2:17][C:14]21[CH2:16][CH2:15]2>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:31]2[C@@H:30]([CH3:33])[C:29](=[O:34])[N:28]3[C@@H:24]([CH2:23][CH2:22][CH2:21][N:19]4[CH2:18][CH2:17][C:14]5([CH2:15][CH2:16]5)[C@H:13]([OH:12])[CH2:20]4)[CH2:25][O:26][C:27]3([CH3:35])[CH2:32]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 76073,4-Dichlorophenyl isocyanateHCID 67093351HCID 67093351, compound

Product 1

HCID 58219407HCID 58219407, compound

Procedure

3,4-Dichlorophenyl isocyanate (28 mg, 0.15 mmol) was added at 0° C. to a solution of (3S,6S)-3-[3-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-6,8a-dimethyl-hexahydro-oxazolo[3,2-a]pyrazin-5-one (50 mg, 0.15 mmol), then the ice bath was removed. After 30 min the reaction mixture was evaporated and the residue chromatographed (SiO2; DCM→DCM/MeOH/25% aq. ammonia solution 90:10:0.25) to pruduce the title compound (57 mg, 73%). Colourless gum, MS: 525.3 (M+H)+.

Workup

  1. customthe ice bath was removed
  2. customAfter 30 min the reaction mixture was evaporated
  3. customthe residue chromatographed (SiO2; DCM→DCM/MeOH/25% aq. ammonia solution 90:10:0.25)

Sources & evidence

ORD record
ord-449b21bb4fff42d4ac917269c09c9016
Source dataset
uspto-grants-2013_06
Patent number
US08471004B2

Reaction notes

Loading…