HCID 23676710, compound → HCID 67185842, compound

HRID 735878Notes

Reaction equation

C([O:3][C:4](=[O:40])[C:5]([N:7]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([NH:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:26])=[CH:21][CH:20]=1)[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1)=[O:6])C.O.O.[OH-].[Li+]>>[CH2:28]([NH:27][C:25]([C:22]1[CH:21]=[CH:20][C:19]([CH2:18][N:7]([C:5](=[O:6])[C:4]([OH:40])=[O:3])[C:8]2[CH:9]=[CH:10][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:13]=2)=[CH:24][CH:23]=1)=[O:26])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Participants

Reactant 2

HCID 23676710HCID 23676710, compound

HCID 67188983HCID 67188983, compound

Product 1

HCID 67185842HCID 67185842, compoundYield 89%

Procedure

The same procedure as employed in the preparation of Example 1 (step c) using ethyl{{4-[(dodecylamino)carbonyl]benzyl}[4-(trifluoromethyl)phenyl]amino}(oxo)acetate and lithium hydroxide dihydrate gave the title compound as a white solid (89%). 1H NMR (DMSO-d6, 300 MHz) δ 8.39 (s, 1H), 7.77 (m, 4H), 7.45 (d, 2H, J=7.9 Hz), 7.27 (d, 2H, J=7.5 Hz), 5.07 (s, 2H), 3.20 (m, 2H), 1.48 (m, 2H), 1.28 (m, 18H), 0.84 (t, 3H, J=5.9 Hz). M−(APCI): 489.2 (M-CO2). HPLC (Condition A), Rt: 6.44 min (HPLC purity: 97.4%).

Workup

customThe same procedure as employed in the preparation of Example 1 (step c)

Sources & evidence

ORD record: ord-d7b64b04bd584d85a9c87161d7f30554
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592477B2

Reaction notes

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