Benzoic acid, 4-fluoro-, ethyl ester → HCID 66818804, compound

HRID 1024787Notes

Reaction equation

[C:1]([O:5][C:6](=[O:33])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:32])[C:16]2[CH:21]=[C:20]([OH:22])[CH:19]=[C:18]([O:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=3)[CH:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH2:34]([O:36][C:37](=[O:45])[C:38]1[CH:43]=[CH:42][C:41](F)=[CH:40][CH:39]=1)[CH3:35]>>[CH2:34]([O:36][C:37](=[O:45])[C:38]1[CH:43]=[CH:42][C:41]([O:22][C:20]2[CH:19]=[C:18]([O:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=3)[CH:17]=[C:16]([C:15](=[O:32])[NH:14][CH:11]3[CH2:12][CH2:13][CH:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:33])[CH2:9][CH2:10]3)[CH:21]=2)=[CH:40][CH:39]=1)[CH3:35]

Participants

Reactant 2

HCID 67976Benzoic acid, 4-fluoro-, ethyl ester

HCID 66818660HCID 66818660, compound

Product 1

HCID 66818804HCID 66818804, compoundYield 68.2%

Procedure

Using 2.0 g (4.4 mmol) of {4-[3-(4-cyano-phenoxy)-5-hydroxy-benzoylamino]-cyclohexyl}-carbamic acid tert-butyl ester and 4-fluoro-benzoic acid ethyl ester (1.2 g, 6.6 mmol) and following the procedure of Example 42(b) afforded 1.8 g of the required product. 1H NMR (DMSO-d6): δ 1.35 (4H, m), 1.4 (9H, s), 1.8 (4H, m), 3.2 (1H, m), 3.68 (1H, m), 4.30 (2H, q), 6.75 (1H, d), 7.20 (5H, m), 7.48 (2H, d), 7.88 (2H, d), 8.00 (2H, d), 8.36 (1H, d).

Sources & evidence

ORD record: ord-bb0711f439114ee096fca5903e3f6ca8
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722930B2

Reaction notes

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