4-(Methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid → HCID 178441255, compound

HRID 76290Notes

Reaction equation

HRID 76290 reaction equation
[C:1]([N:5]1[CH:9]=[C:8]([CH2:10][CH2:11][CH2:12][CH3:13])[C:7](=[NH:14])[S:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:15][O:16][C:17]([C:19]12[CH2:26][CH2:25][C:22]([C:27](O)=[O:28])([CH2:23][CH2:24]1)[CH2:21][CH2:20]2)=[O:18]>>[CH2:10]([C:8]1=[CH:9][N:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[S:6]/[C:7]/1=[N:14]\[C:27]([C:22]12[CH2:25][CH2:26][C:19]([C:17]([O:16][CH3:15])=[O:18])([CH2:20][CH2:21]1)[CH2:24][CH2:23]2)=[O:28])[CH2:11][CH2:12][CH3:13]

Participants

3

Reactant 2

HCID 110420624-(Methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acidHCID 668672282-tert-Butyl-4-butylisothiazol-5(2H)-imine

Product 1

HCID 178441255HCID 178441255, compound

Procedure

The product from Example 92B and 4-(methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid (Oakwood) were processed using the method described in Example 92C to afford the title compound. 1H NMR (DMSO-d6) δ 0.91 (t, J=7.3 Hz, 3H), 1.23-1.36 (m, 2H), 1.58 (s, 9H), 1.58-1.66 (m, 2H), 1.70-1.83 (m, 12 H), 2.61-2.66 (m, 2H), 3.58 (s, 3H), 8.49 (s, 1H). (ESI+) m/z 407 (M+H)+. Anal. calcd. for C22H34N2O3S: C, 64.99; H, 8.43; N, 6.89. Found: C, 64.65; H, 8.24; N, 6.72.

Sources & evidence

ORD record
ord-82782e70f799494ebd7bab0ca87e8fd8
Source dataset
uspto-grants-2014_09
Patent number
US08835475B2

Reaction notes

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