Trifluoroacetic acid → HCID 178464333, compound

HRID 2389187Notes

Reaction equation

HRID 2389187 reaction equation
[NH2:1][C:2]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][C@H:20]3[CH2:25][CH2:24][C@H:23]([C:26]([F:29])([F:28])[F:27])[CH2:22][CH2:21]3)[CH:15]=2)[CH:10]=1)([CH3:8])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].C(O)(C(F)(F)F)=O.[N+](C(C1C=CC2C(=CC=C(O[C@H]3CC[C@@H](C(F)(F)F)CC3)C=2)C=1)(C)CCC(O)=O)([O-])=O>>[NH2:1][C:2]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][C@H:20]3[CH2:25][CH2:24][C@@H:23]([C:26]([F:27])([F:28])[F:29])[CH2:22][CH2:21]3)[CH:15]=2)[CH:10]=1)([CH3:8])[CH2:3][CH2:4][C:5]([OH:7])=[O:6]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 178447444HCID 178447444, compoundHCID 178464334HCID 178464334, compound

Product 1

HCID 178464333HCID 178464333, compoundYield 21%

Procedure

4-Amino-4-[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 21% yield as TFA salt, using 4-nitro-4-[6-(cis-4-trifluoromethyl-cyclohexyloxy)-naphthalen-2-yl]-pentanoic acid as the starting material. MS: m/z=432.20 [M+Na]+. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm: 7.64-7.75 (m, 3H), 7.35 (dd, J=8.8, 2.0 Hz, 1H), 7.14 (dd, J=8.9, 2.1 Hz, 1H), 7.08 (s, 1H), 4.67 (br. s., 1H), 2.22-2.41 (m, 2H), 1.98-2.20 (m, 5H), 1.63-1.80 (m, 7H), 1.48-1.61 (m, 2H).

Sources & evidence

ORD record
ord-6089dd1e73134a9a87f52add731bbcea
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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