HCID 178445728, compound → HCID 178445752, compound

HRID 1036486Notes

Reaction equation

N[C@@](C1C=CC2C(=CC=C(O[C@H]3CC[C@H](C(C)(C)C)CC3)C=2C2C=CC(OC(F)(F)F)=CC=2)C=1)(C)CO.[C:38]([C@H:42]1[CH2:47][CH2:46][C@H:45]([O:48][C:49]2[C:50]([C:66]3[CH:71]=[CH:70][C:69]([S:72]([CH3:75])(=[O:74])=[O:73])=[CH:68][CH:67]=3)=[C:51]3[C:56](=[CH:57][CH:58]=2)[CH:55]=[C:54]([C@:59]2([CH3:65])[CH2:63][O:62]C(=O)[NH:60]2)[CH:53]=[CH:52]3)[CH2:44][CH2:43]1)([CH3:41])([CH3:40])[CH3:39]>>[NH2:60][C@@:59]([C:54]1[CH:53]=[CH:52][C:51]2[C:56](=[CH:57][CH:58]=[C:49]([O:48][C@H:45]3[CH2:44][CH2:43][C@H:42]([C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:47][CH2:46]3)[C:50]=2[C:66]2[CH:71]=[CH:70][C:69]([S:72]([CH3:75])(=[O:73])=[O:74])=[CH:68][CH:67]=2)[CH:55]=1)([CH3:65])[CH2:63][OH:62]

Participants

Reactant 2

HCID 178445728HCID 178445728, compound

HCID 178445751HCID 178445751, compound

Product 1

HCID 178445752HCID 178445752, compoundYield 36%

Procedure

(R)-2-amino-2-(6-(trans-4-tert-butylcyclohexyloxy)-5-(4-(methylsulfonyl)phenyl)naphthalen-2-yl)propan-1-ol was synthesized as per (R)-2-amino-2-(6-(trans-4-tert-butylcyclohexyloxy)-5-(4-(trifluoromethoxy)phenyl)naphthalen-2-yl)propan-1-ol (Example 221) in 36% yield using (R)-4-(6-(trans-4-tert-butylcyclohexyloxy)-5-(4-(methylsulfonyl)phenyl)naphthalen-2-yl)-4-methyloxazolidin-2-one as starting material. MS: m/z 493.26 [M−16]+. 1H NMR (MeOD) δ: 8.03-8.12 (m, 2H), 7.91-7.99 (m, 2H), 7.55-7.63 (m, 2H), 7.42-7.53 (m, 2H), 7.32-7.40 (m, 1H), 4.21 (br. s., 1H), 3.58-3.76 (m, 2H), 3.25 (br. s., 3H), 2.05 (br. s., 2H), 1.80 (br. s., 2H), 1.52 (br. s., 3H), 1.05-1.25 (m, 4H), 0.90-1.04 (m, 1H), 0.87 (br. s., 9H)

Sources & evidence

ORD record: ord-edf0609b7d5c493ab753993cd738868e
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546359B2

Reaction notes

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