Hydrochloric Acid → HCID 178465496, compound

HRID 2389179Notes

Reaction equation

N[C@@](C1C=CC2C(=CC=C(O[C@H]3CC[C@H](C(F)(F)F)CC3)C=2)C=1)(C)COP(=O)(O)O.Cl.C(OC(=O)[NH:38][C@:39]([CH3:79])([C:54]1[CH:63]=[CH:62][C:61]2[C:56](=[CH:57][CH:58]=[C:59]([O:68][C@H:69]3[CH2:74][CH2:73][C@H:72]([C:75]([F:78])([F:77])[F:76])[CH2:71][CH2:70]3)[C:60]=2[C:64]([F:67])([F:66])[F:65])[CH:55]=1)[CH2:40][O:41][P:42]([O:49]C(C)(C)C)([O:44]C(C)(C)C)=[O:43])(C)(C)C>>[NH2:38][C@@:39]([C:54]1[CH:63]=[CH:62][C:61]2[C:56](=[CH:57][CH:58]=[C:59]([O:68][C@H:69]3[CH2:74][CH2:73][C@H:72]([C:75]([F:78])([F:76])[F:77])[CH2:71][CH2:70]3)[C:60]=2[C:64]([F:67])([F:66])[F:65])[CH:55]=1)([CH3:79])[CH2:40][O:41][P:42](=[O:43])([OH:44])[OH:49]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 178453570HCID 178453570, compound

HCID 178465498HCID 178465498, compound

Product 1

HCID 178465496HCID 178465496, compoundYield 89%

Procedure

Phosphoric acid mono-{(R)-2-amino-2-[5-trifluoromethyl-6-(trans-4-trifluoromethyl-cyclohexyloxy)-naphthalen-2-yl]-propyl}ester was synthesized as per Phosphoric acid mono-{(R)-2-amino-2-[6-(trans-4-trifluoromethyl-cyclohexyloxy)-naphthalen-2-yl]-propyl} ester (Example 263) in 89% yield as HCl salt, using {(R)-2-(Di-tert-butoxy-phosphoryloxy)-1-methyl-1-[5-trifluoromethyl-6-(trans-4-trifluoromethyl-cyclohexyloxy)-naphthalen-2-yl]-ethyl}-carbamic acid tert-butyl ester as starting material. MS: m/z=516.30 [M+H]+. 1H NMR (400 MHz, METHANOL-d4) δ ppm: 8.26 (dd, J=9.4, 1.4 Hz, 1H), 8.16 (d, J=9.3 Hz, 1H), 8.02 (d, J=2.3 Hz, 1H), 7.72 (dd, J=9.3, 2.3 Hz, 1H), 7.63 (d, J=9.3 Hz, 1H), 4.55-4.66 (m, 1H), 4.31 (dd, J=11.3, 4.8 Hz, 1H), 4.17 (dd, J=11.2, 5.1 Hz, 1H), 2.20-2.34 (m, 3H), 2.02-2.12 (m, 2H), 1.86 (s, 3H), 1.49-1.72 (m, 4H).

Sources & evidence

ORD record: ord-733d6f9c19304515926b88883667d5a8
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08269043B2

Reaction notes

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