2-Chloro-4-isocyanato-3-methylbenzonitrile → (7S,7aR)-2-Chloro-4-(7-hydroxy-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl)-3-methylbenzonitrile

HRID 501566Notes

Reaction equation

HRID 501566 reaction equation
Cl.CO[C:4]([C@@H:6]1[C@@H:10]([OH:11])[CH2:9][CH2:8][NH:7]1)=[O:5].[Cl:12][C:13]1[C:20]([CH3:21])=[C:19]([N:22]=[C:23]=[O:24])[CH:18]=[CH:17][C:14]=1[C:15]#[N:16]>>[Cl:12][C:13]1[C:20]([CH3:21])=[C:19]([N:22]2[C:4](=[O:5])[C@H:6]3[C@@H:10]([OH:11])[CH2:9][CH2:8][N:7]3[C:23]2=[O:24])[CH:18]=[CH:17][C:14]=1[C:15]#[N:16]

Participants

3

Reactant 2

HCID 167318492-Chloro-4-isocyanato-3-methylbenzonitrileHCID 66605223methyl (2S,3S)-3-hydroxypyrrolidine-2-carboxylate hydrochloride

Product 1

HCID 59754345(7S,7aR)-2-Chloro-4-(7-hydroxy-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl)-3-methylbenzonitrile

Procedure

The title compound was prepared from compound 1A and compound 23E in a manner similar to that described in Example 19. mp 237-238° C.; HPLC: 100% at 2.11 and 2.36 min (retention time) (Conditions: Phenomenex Luna C18 (4.6×50 mm); Eluted with 0% to 100% B, 4 min gradient (A=90% H2O-10% MeOH-0.1% H3PO4 and B=10% H2O-90% MeOH-0.1% H3PO4); Flow rate at 4 mL/min. UV detection at 220 nm). Chiral HPLC: retention time=15.9 min (100%); Conditions: OD (4.6×250 mm); Eluted with 20% isopropanol in hexane for 30 min at 1 mL/min, MS (ES) m/z 306 [M+1]+.

Workup

  1. washEluted with 0% to 100% B, 4 min gradient (A=90% H2O-10% MeOH-0.1% H3PO4 and B=10% H2O-90% MeOH-0.1% H3PO4)
  2. washEluted with 20% isopropanol in hexane for 30 min at 1 mL/min, MS (ES) m/z 306 [M+1]+

Sources & evidence

ORD record
ord-dae5d0abfe0f48a6b23ac19c38205aeb
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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