[(1S,2S,4S)-Bicyclo[2.2.1]hept-5-en-2-yl]acetic acid → HCID 67160943, compound

HRID 469579Notes

Reaction equation

HRID 469579 reaction equation
[NH2:1][N:2]1[N:11]=[C:10]([CH:12]2[CH2:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:16].[C@@H:17]12[CH2:23][C@@H:20]([CH:21]=[CH:22]1)[CH2:19][C@H:18]2[CH2:24][C:25](O)=[O:26]>>[C@@H:17]12[CH2:23][C@@H:20]([CH:21]=[CH:22]1)[CH2:19][C@H:18]2[CH2:24][C:25]([NH:1][N:2]1[N:11]=[C:10]([CH:12]2[CH2:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:16])=[O:26]

Participants

3

Reactant 2

HCID 28063363[(1S,2S,4S)-Bicyclo[2.2.1]hept-5-en-2-yl]acetic acidHCID 67162274HCID 67162274, compound

Product 1

HCID 67160943HCID 67160943, compound

Procedure

The product of Example 67A and 2-((1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl)acetic acid were processed using a method similar to that described in Example 17C to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.13 (s, 1H), 8.34-8.28 (m, 1H), 8.00-7.93 (m, 1H), 7.92-7.83 (m, 2H), 6.22 (dd, J=5.7, 3.0, 1H), 6.07 (dd, J=5.7, 2.9, 1H), 4.10-3.99 (m, 1H), 2.91 (s, 1H), 2.79 (s, 1H), 2.49-2.42 (m, 1H), 2.41-2.22 (m, 4H), 2.14-2.02 (m, 3H), 1.95-1.87 (m, 1H), 1.86-1.77 (m, 1H), 1.39-1.31 (m, 1H), 1.26 (d, J=8.0, 1H), 0.61 (ddd, J=11.5, 4.2, 2.6, 1H); MS (ESI) m/z 350 (M+H)+.

Sources & evidence

ORD record
ord-1d3aa621f56546fd9adb320aa4fbef77
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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