2-((1S,2S,5S)-6,6-Dimethylbicyclo[3.1.1]heptan-2-yl)acetic acid → tert-butyl{[3-({[(1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]acetyl}amino)-4-oxo-3,4-dihydrophthalazin-1-yl]methyl}carbamate

HRID 535543Notes

Reaction equation

HRID 535543 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[N:11]([NH2:20])[N:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:22][C:23]1([CH3:34])[C@H:28]2[CH2:29][C@@H:24]1[CH2:25][CH2:26][C@H:27]2[CH2:30][C:31](O)=[O:32]>>[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[N:11]([NH:20][C:31](=[O:32])[CH2:30][C@@H:27]2[CH2:26][CH2:25][C@H:24]3[CH2:29][C@@H:28]2[C:23]3([CH3:22])[CH3:34])[N:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 671611162-((1S,2S,5S)-6,6-Dimethylbicyclo[3.1.1]heptan-2-yl)acetic acidHCID 131731940Tert-butyl(3-amino-4-oxo-3,4-dihydrophthalazin-1-yl)methylcarbamate

Product 1

HCID 131731942tert-butyl{[3-({[(1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]acetyl}amino)-4-oxo-3,4-dihydrophthalazin-1-yl]methyl}carbamate

Procedure

The product of Example 41B and 2-[(1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]acetic acid (Eigenmann, G. W.; Arnold, R. T. JACS 1959, 81, 3440-2) were treated using a method similar to that described in Example 56 to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 11.24 (s, 1H), 8.36-8.28 (m, 1H), 8.10 (d, J=7.8, 1H), 7.98 (dd, J=11.1, 4.1, 1H), 7.90 (t, J=7.1, 1H), 7.40 (s, 1H), 4.45 (d, J=5.7, 2H), 2.41-2.29 (m, 3H), 2.07-1.80 (m, 5H), 1.64-1.47 (m, 1H), 1.43-1.29 (m, 10H), 1.21 (s, 3H), 1.07 (s, 3H), 0.91 (d, J=9.5, 1H). MS (ESI+) M/Z 472 (M+NH4)+.

Sources & evidence

ORD record
ord-a0415bca5f1346a193093e3b2522e0b6
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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