[(1S,2S,4S)-Bicyclo[2.2.1]hept-5-en-2-yl]acetic acid → HCID 70975752, compound

HRID 535489Notes

Reaction equation

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

Participants

Reactant 2

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

HCID 70975803HCID 70975803, compound

Product 1

HCID 70975752HCID 70975752, compound

Procedure

The product from Example 10B and 2-((1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl)acetic acid was processed using a method similar to that described in Example 10C to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.31 (s, 1H), 8.41 (dd, J=7.8, 1.4 Hz, 1H), 8.18 (d, J=8.0 Hz, 1H), 7.92-8.10 (m, 2H), 7.80 (dd, J=5.1, 1.1 Hz, 1H), 7.65 (dd, J=3.6, 1.1 Hz, 1H), 7.29 (dd, J=5.1, 3.6 Hz, 1H), 6.23 (dd, J=5.7, 3.0 Hz, 1H), 6.07 (dd, J=5.7, 2.8 Hz, 1H), 2.89-2.92 (m, 1H), 2.77-2.81 (m, 1H), 2.42-2.50 (m, 1H), 2.10 (dd, J=14.3, 7.9 Hz, 1H), 2.08 (dd, J=14.1, 8.0 Hz, 1H), 1.91 (ddd, J=11.5, 9.0, 3.8 Hz, 1H), 1.34-1.37 (m, 1H), 1.27 (d, J=8.1 Hz, 1H), 0.61 (ddd, J=11.5, 4.3, 2.5 Hz, 1H); MS (APCI) M/Z 392 (M+H)+.

Sources & evidence

ORD record: ord-be6918311a3a4340808dbf90302d43e1
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859549B2

Reaction notes

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