(7R,7aS)-4-(7-Hydroxy-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl)-5,6,7,8-tetrahydronaphthalene-1-carbonitrile → HCID 68457860, compound

HRID 501587Notes

Reaction equation

HRID 501587 reaction equation
C(C1C2N=[N:10][S:11]C=2C(N)=CC=1)#N.[N:13](C1C2CCCCC=2C(C#N)=CC=1)=C=O.[OH:28][C@H:29]1[C@@H:36]2[N:32]([C:33](=[O:50])[N:34]([C:38]3[C:47]4CCCC[C:42]=4[C:41]([C:48]#[N:49])=[CH:40][CH:39]=3)[C:35]2=[O:37])[CH2:31][CH2:30]1>>[OH:28][C@H:29]1[C@H:36]2[N:32]([C:33](=[O:50])[N:34]([C:38]3[C:47]4[C:42](=[N:13][S:11][N:10]=4)[C:41]([C:48]#[N:49])=[CH:40][CH:39]=3)[C:35]2=[O:37])[CH2:31][CH2:30]1

Participants

4

Reactant 3

HCID 9904811(7R,7aS)-4-(7-Hydroxy-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl)-5,6,7,8-tetrahydronaphthalene-1-carbonitrileHCID 21875161HCID 21875161, compoundHCID 597543044-Isocyanato-5,6,7,8-tetrahydronaphthalene-1-carbonitrile

Product 1

HCID 68457860HCID 68457860, compound

Procedure

The title compound (12.2 mg) was prepared from compound 50A by procedures analogous to those described in Experiment 2E and 2F. HPLC: 99% at 1.57 min (retention time) (Conditions: Phenom. Luna. (4.6×50 mm); Eluted with 0% to 100% B, 4 min gradient, 1 min hold. (A=90% H2O-10% MeOH-0.1% TFA and B=10% H2O-90% MeOH-0.1% TFA); Flow rate at 4.0 ml/min UV detection at 220 nm). Chiral HPLC: retention time=22.68 min (98%); Conditions: OD (4.6×250 mm); Eluted with 25% isopropanol in hexane for 30 min at 1 mL/min; MS (ES) m/z 316 [M+1]+.

Workup

  1. washEluted with 0% to 100% B, 4 min gradient, 1 min hold
  2. washEluted with 25% isopropanol in hexane for 30 min at 1 mL/min

Sources & evidence

ORD record
ord-fcb7e26499d64a7cbe786f5cabe3c3d8
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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