Ammonia → HCID 178441303, compound

HRID 1888684

Reaction equation

HRID 1888684 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].[C:15]([OH:28])(=O)[C:16]1([CH2:26][CH2:25][CH:21]([C:22](O)=[O:23])[C:18]1([CH3:20])[CH3:19])[CH3:17].[NH3:29]>CO>[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:22]([C@H:21]1[CH2:25][CH2:26][C@@:16]([CH3:17])([C:15]([NH2:29])=[O:28])[C:18]1([CH3:20])[CH3:19])=[O:23])[CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 214911,2,2-Trimethyl-1,3-cyclopentanedicarboxylic acidHCID 668672282-tert-Butyl-4-butylisothiazol-5(2H)-imine

Product 1

HCID 178441303HCID 178441303, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Example 92B and the (+) camphoric acid (Aldrich) were processed using the method described in Example 170 except that the methanol used to trap the intermediate was saturated with ammonia solution instead of methanol to afford the title compound. 1H NMR (DMSO-d6) δ 0.50 (s, 3H), 0.90 (t, J=7.2 Hz, 3H), 1.19 (s, 3H), 1.23-1.44 (m, 3H), 1.26 (s, 3H), 1.57 (s, 9H), 1.57-1.71 (m, 3H), 1.93-2.06 (m, 1H), 2.71-2.82 (m, 1H), 2.62-2.69 (m, 3H), 7.01 (s, 1H), 6.75 (s, 1H), 8.50 (s, 1H). MS (ESI+) m/z 394 (M+H)+. Anal. calcd. for C11H35N3O2S: C, 64.08; H, 8.96; N, 10.68. Found: C, 64.26; H, 9.10; N, 10.65.

Workup

  1. customused to trap

Sources & evidence

ORD record
ord-a7405d8924b6428ca7d618916c83d8e4
Source dataset
uspto-grants-2013_08
Patent number
US08501794B2

Linked notes

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