HCID 178445779, compound → HCID 178464332, compound

HRID 1036471Notes

Reaction equation

NC(C1C=CC2C(=CC=C(O[C@H]3CC[C@H](C(C)(C)C)CC3)C=2C(F)(F)F)C=1)CCC(O)=O.[C:33]([C@H:37]1[CH2:42][CH2:41][C@H:40]([O:43][C:44]2[CH:45]=[C:46]3[C:51](=[CH:52][CH:53]=2)[CH:50]=[C:49]([C:54]([N+:61]([O-])=O)([CH3:60])[CH2:55][CH2:56][C:57]([OH:59])=[O:58])[CH:48]=[CH:47]3)[CH2:39][CH2:38]1)([CH3:36])([CH3:35])[CH3:34]>>[NH2:61][C:54]([C:49]1[CH:48]=[CH:47][C:46]2[C:51](=[CH:52][CH:53]=[C:44]([O:43][C@H:40]3[CH2:41][CH2:42][C@H:37]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:38][CH2:39]3)[CH:45]=2)[CH:50]=1)([CH3:60])[CH2:55][CH2:56][C:57]([OH:59])=[O:58]

Participants

Reactant 2

HCID 178445779HCID 178445779, compound

HCID 178447443HCID 178447443, compound

Product 1

HCID 178464332HCID 178464332, compoundYield 3%

Procedure

4-amino-4-(6-(trans-4-tert-butylcyclohexyloxy)naphthalen-2-yl)pentanoic acid was synthesized as per 4-amino-4-(6-(trans-4-tert-butylcyclohexyloxy)-5-(trifluoromethyl)naphthalen-2-yl)butanoic acid (Example 203) in 3% yield using 4-(6-(trans-4-tert-butylcyclohexyloxy)naphthalen-2-yl)-4-nitropentanoic acid as starting material. MS: m/z=381.53 [M−NH2]+. 1H NMR (MeOD) δ: 7.91 (d, J=8.7 Hz, 1H), 7.83-7.88 (m, 2H), 7.55 (dd, J=8.7, 1.9 Hz, 1H), 7.31 (d, J=2.3 Hz, 1H), 7.21 (dd, J=9.1, 2.3 Hz, 1H), 4.34-4.47 (m, 1H), 2.69 (s, 3H), 2.40-2.57 (m, 2H), 2.23-2.39 (m, 3H), 2.06-2.19 (m, 1H), 1.91-2.01 (m, 2H), 1.88 (s, 2H), 1.39-1.55 (m, 2H), 1.11-1.39 (m, 3H), 0.96 (s, 9H)

Sources & evidence

ORD record: ord-ec64271f18914e93be32e175bfae2e17
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546359B2

Reaction notes

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