Acetic Acid → HCID 46196245, compound

HRID 2389093Notes

Reaction equation

C(OC(=O)[NH:7][C@@:8]([C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[C:29]([O:38][CH:39]3[CH2:44][CH2:43][CH:42]([CH:45]4[CH2:49][CH2:48][CH2:47][CH2:46]4)[CH2:41][CH2:40]3)[C:30]=2[C:34]([F:37])([F:36])[F:35])[CH:25]=1)([CH3:23])[CH2:9][O:10][P:11]([O:18]C(C)(C)C)([O:13]C(C)(C)C)=[O:12])(C)(C)C.Cl.O.C(O)(=O)C>>[NH2:7][C@@:8]([C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[C:29]([O:38][CH:39]3[CH2:44][CH2:43][CH:42]([CH:45]4[CH2:49][CH2:48][CH2:47][CH2:46]4)[CH2:41][CH2:40]3)[C:30]=2[C:34]([F:35])([F:36])[F:37])[CH:25]=1)([CH3:23])[CH2:9][O:10][P:11](=[O:12])([OH:13])[OH:18]

Participants

Reactant 4

HCID 176Acetic Acid

HCID 313Hydrochloric Acid

HCID 962Water

HCID 67413236HCID 67413236, compound

Product 1

HCID 46196245HCID 46196245, compoundYield 103.5%

Procedure

[(R)-1-[6-(4-Cyclopentyl-cyclohexyloxy)-5-trifluoromethyl-naphthalen-2-yl]-2-(di-tert-butoxy-phosphoryloxy)-1-methyl-ethyl]-carbamic acid tert-butyl ester (11 mg, 0.000015 mol) was added 12 M of hydrogen chloride in water (1 mL, 0.01 mol; Supplier=Aldrich) and acetic acid (1 mL, 0.02 mol) and the solution was stirred for 1.5 h at RT. All solvent was then removed inder reduced pressure and the residue was dried on high-vac over night to give the desired product 8 mg was a white HCl salt (98%). ESI-MS: 499 (M-16)+. 1H NMR (400 MHz, DMSO-d6) δ=8.19-8.07 (m, 1 H), 7.84 (d, J=9.0 Hz, 1 H), 7.63-7.42 (m, 2 H), 7.22 (dd, J=5.0, 9.0 Hz, 1 H), 5.10 (br. s., 1 H), 4.32-4.11 (m, 1 H), 3.72 (m, 2 H), 2.18-1.98 (m, 2 H), 1.92-0.71 (m, 21 H)

Workup

customAll solvent was then removed inder reduced pressure
customthe residue was dried on high-vac over night

Sources & evidence

ORD record: ord-4e7f10a58bad4094bb03e1de998f9ae9
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08269043B2

Reaction notes

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