[(1S,2S,4S)-Bicyclo[2.2.1]hept-5-en-2-yl]acetic acid → HCID 67160083, compound

HRID 469647Notes

Reaction equation

HRID 469647 reaction equation
[NH2:1][N:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=2[CH3:19])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:20].[C@@H:21]12[CH2:27][C@@H:24]([CH:25]=[CH:26]1)[CH2:23][C@H:22]2[CH2:28][C:29](O)=[O:30]>>[C@@H:21]12[CH2:27][C@@H:24]([CH:25]=[CH:26]1)[CH2:23][C@H:22]2[CH2:28][C:29]([NH:1][N:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=2[CH3:19])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:20])=[O:30]

Participants

3

Reactant 2

HCID 28063363[(1S,2S,4S)-Bicyclo[2.2.1]hept-5-en-2-yl]acetic acidHCID 67161053HCID 67161053, compound

Product 1

HCID 67160083HCID 67160083, compound

Procedure

The product of Example 159A and 2-[(1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl]acetic acid were treated using a method similar to that described in Example 17C to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.26 (s, 1H), 8.37-8.40 (m, 1H), 7.85-7.97 (m, 2H), 7.26-7.32 (m, 1H), 7.20-7.25 (m, 2H), 7.16-7.20 (m, 1H), 6.21 (dd, J=5.7, 2.9 Hz, 1H), 6.05 (dd, J=5.7, 2.9 Hz, 1H), 2.86-2.91 (m, 1H), 2.76-2.81 (m, 1H), 2.41-2.49 (m, 1H), 2.38 (s, 3H), 2.01-2.12 (m, 2H), 2.06 (s, 3H), 1.86-1.93 (m, 1H), 1.33 (dd, J=7.9, 2.5 Hz, 1H), 1.26 (d, J=8.1 Hz, 1H), 0.59 (ddd, J=11.5, 4.3, 2.5 Hz, 1H); MS (APCI+) M/Z 400 (M+H)+.

Sources & evidence

ORD record
ord-ee17f53df4f34b159f93cd219cdbfb2d
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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