Hydrochloric Acid → HCID 46196357, compound

HRID 1036463Notes

Reaction equation

CC1(C)[O:7][CH2:6][C:5]([NH:29]C(=O)OC(C)(C)C)([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=4)[CH:14]=3)[CH:9]=2)[CH2:4][O:3]1.CO.Cl.O>>[NH2:29][C:5]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:27])[F:28])[CH:20]=3)[CH:14]=2)[CH:9]=1)([CH2:6][OH:7])[CH2:4][OH:3]

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 962Water

HCID 86642897HCID 86642897, compound

Product 1

HCID 46196357HCID 46196357, compoundYield 100%

Conditions

Temperature: 50 °C

Procedure

tert-Butyl 2,2-Dimethyl-5-(6-(3-(trifluoromethyl)phenoxy)naphthalen-2-yl)-1,3-dioxan-5-ylcarbamate (35.0 mg, 0.0000676 mol) was dissolved in methanol (2 mL, 0.06 mol), followed by 2 M hydrogen chloride in water (2 mL, 0.004 mol). The reaction mixture was then heated at 50° C. for 3 hours. All solvents were removed to give a pure product (23 mg, 100%). 1H NMR (MeOD) δ: 8.00 (d, J=9.0 Hz, 1H), 7.96 (s, 1H), 7.90 (d, J=8.8 Hz, 1H), 7.54-7.64 (m, 2H), 7.42-7.48 (m, 2H), 7.24-7.37 (m, 3H), 4.05-4.13 (m, 2H), 3.94-4.03 (m, 2H). MS (M+1): 378.20.

Workup

customAll solvents were removed

Sources & evidence

ORD record: ord-5ce1d70284bb488baa6c4e78523526a1
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546359B2

Reaction notes

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