HCID 178447440, compound → HCID 178464329, compound

HRID 1036475Notes

Reaction equation

NC(C1C=CC2C(=CC=C(O[C@H]3CC[C@H](C(C)(C)C)CC3)C=2)C=1)(C)CCC(O)=O.[C:30]([C@H:34]1[CH2:39][CH2:38][C@H:37]([O:40][C:41]2[C:42]([C:61]([F:64])([F:63])[F:62])=[C:43]3[C:48](=[CH:49][CH:50]=2)[CH:47]=[C:46]([C:51]([N+:58]([O-])=O)([CH3:57])[CH2:52][CH2:53][C:54]([OH:56])=[O:55])[CH:45]=[CH:44]3)[CH2:36][CH2:35]1)([CH3:33])([CH3:32])[CH3:31]>>[NH2:58][C:51]([C:46]1[CH:45]=[CH:44][C:43]2[C:48](=[CH:49][CH:50]=[C:41]([O:40][C@H:37]3[CH2:36][CH2:35][C@H:34]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:39][CH2:38]3)[C:42]=2[C:61]([F:63])([F:64])[F:62])[CH:47]=1)([CH3:57])[CH2:52][CH2:53][C:54]([OH:56])=[O:55]

Participants

Reactant 2

HCID 178447440HCID 178447440, compound

HCID 178464332HCID 178464332, compound

Product 1

HCID 178464329HCID 178464329, compoundYield 26%

Procedure

4-amino-4-(6-(trans-4-tert-butylcyclohexyloxy)-5-(trifluoromethyl)naphthalen-2-yl)pentanoic acid was synthesized as per 4-amino-4-(6-(trans-4-tert-butylcyclohexyloxy)naphthalen-2-yl)pentanoic acid (Example 207) in 26% yield using 4-(6-(trans-4-tert-butylcyclohexyloxy)-5-(trifluoromethyl)naphthalen-2-yl)-4-nitropentanoic acid as starting material. MS: m/z=449.71 [M−NH2]+. 1H NMR (MeOD) δ: 8.25-8.31 (m, 1H), 8.14 (d, J=9.3 Hz, 1H), 7.96 (d, J=2.3 Hz, 1H), 7.69 (dd, J=9.3, 2.5 Hz, 7.60 (d, J=9.3 Hz, 1H), 4.46-4.56 (m, 1H), 2.65-2.70 (m, 3H), 2.37-2.54 (m, 2H), 2.18-2.35 (m, 2H), 2.07-2.18 (m, 2H), 1.95 (br. s., 2H), 1.87 (s, 2H), 1.50 (br. s., 2H), 1.19-1.34 (m, 2H), 1.07-1.18 (m, 1H), 0.88-0.95 (m, 9H)

Sources & evidence

ORD record: ord-7d993e9df4c34670b1404452e3bad533
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546359B2

Reaction notes

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