Trifluoroacetic acid → HCID 178464330, compound

HRID 2389192Notes

Reaction equation

HRID 2389192 reaction equation
NC(C1C=CC2C(=CC=C(O[C@H]3CC[C@H](C(F)(F)F)CC3)C=2)C=1)(C)CCC(O)=O.C(O)(C(F)(F)F)=O.[N+:37]([C:40]([C:47]1[CH:56]=[CH:55][C:54]2[C:49](=[CH:50][CH:51]=[C:52]([O:61][C@H:62]3[CH2:67][CH2:66][C@@H:65]([C:68]([F:71])([F:70])[F:69])[CH2:64][CH2:63]3)[C:53]=2[C:57]([F:60])([F:59])[F:58])[CH:48]=1)([CH3:46])[CH2:41][CH2:42][C:43]([OH:45])=[O:44])([O-])=O>>[NH2:37][C:40]([C:47]1[CH:56]=[CH:55][C:54]2[C:49](=[CH:50][CH:51]=[C:52]([O:61][C@H:62]3[CH2:63][CH2:64][C@@H:65]([C:68]([F:69])([F:70])[F:71])[CH2:66][CH2:67]3)[C:53]=2[C:57]([F:59])([F:60])[F:58])[CH:48]=1)([CH3:46])[CH2:41][CH2:42][C:43]([OH:45])=[O:44]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 178447441HCID 178447441, compoundHCID 178464334HCID 178464334, compound

Product 1

HCID 178464330HCID 178464330, compoundYield 46%

Procedure

4-Amino-4-[5-trifluoromethyl-6-(cis-4-trifluoromethyl-cyclohexyloxy)-naphthalen-2-yl]-pentanoic acid was synthesized as per 4-amino-4-[6-(trans-4-trifluoromethyl-cyclohexyloxy)-naphthalen-2-yl]-pentanoic acid (Example 282) in 46% yield (as TFA salt), using 4-nitro-4-[5-trifluoromethyl-6-(cis-4-trifluoromethyl-cyclohexyloxy)-naphthalen-2-yl]-pentanoic acid as starting material. MS: m/z=500.10 [M+Na]+. 1H NMR (400 MHz, to DMSO-d6) δ ppm: 12.23 (br. s., 8.52 (br. s., 3H), 8.23 (d, J=9.3 Hz, 1H), 8.14 (d, J=8.0 Hz, 1H), 8.04 (d, J=1.8 Hz, 1H), 7.77 (dd, J=9.3, 2.0 Hz, 1H), 7.71 (d, J=9.3 Hz, 1H), 5.07-5.13 (br. s., 1H), 2.39-2.59 (m, 2H obscured), 2.21-2.34 (m, 2H), 1.93-2.17 (m, 4H), 1.56-1.78 (m, 9H).

Sources & evidence

ORD record
ord-3680b331493448bfacefe5d98282e5cd
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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