[(1S,2S,4S)-Bicyclo[2.2.1]hept-5-en-2-yl]acetic acid → HCID 70975747, compound

HRID 535493Notes

Reaction equation

HRID 535493 reaction equation
[NH2:1][N:2]1[N:11]=[C:10]([C:12]2[S:13][CH:14]=[CH:15][C:16]=2[CH3:17])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:18].[C@@H:19]12[CH2:25][C@@H:22]([CH:23]=[CH:24]1)[CH2:21][C@H:20]2[CH2:26][C:27](O)=[O:28]>>[C@@H:19]12[CH2:25][C@@H:22]([CH:23]=[CH:24]1)[CH2:21][C@H:20]2[CH2:26][C:27]([NH:1][N:2]1[N:11]=[C:10]([C:12]2[S:13][CH:14]=[CH:15][C:16]=2[CH3:17])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:18])=[O:28]

Participants

3

Reactant 2

HCID 28063363[(1S,2S,4S)-Bicyclo[2.2.1]hept-5-en-2-yl]acetic acidHCID 70976322HCID 70976322, compound

Product 1

HCID 70975747HCID 70975747, compound

Procedure

The product from Example 14B 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), 8.38-8.40 (m, 1H), 7.89-8.05 (m, 2H), 7.72 (d, J=5.1 Hz, 1H), 7.62-7.65 (m, 1H), 7.12 (d, J=5.1 Hz, 1H), 6.22 (dd, J=5.7, 3.0 Hz, 1H), 6.06 (dd, J=5.7, 2.8 Hz, 1H), 2.88-2.90 (m, 1H), 2.77-2.79 (m, 1H), 2.42-2.52 (m, 1H), 2.10 (s, 3H), 2.08 (m, 2H), 1.90 (ddd, J=11.5, 9.1, 3.7 Hz, 1H), 1.33-1.36 (m, 1H), 1.26 (d, J=8.0 Hz, 1H), 0.60 (ddd, J=11.5, 4.3, 2.5 Hz, 1H); MS (APCI) M/Z 392 (M+H)+.

Sources & evidence

ORD record
ord-387f80968921409c8dd2f4367f578709
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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