Hydrochloric Acid → 3-(Trifluoromethyl)phenyl (5',6'-dioxo-5',6'-dihydrospiro[cyclohexane-1,2'-naphtho[1,2-b][1,4]oxathiin]-4-yl)carbamate

HRID 1665315Notes

Reaction equation

HRID 1665315 reaction equation
Cl.[NH2:2][CH:3]1[CH2:23][CH2:22][C:6]2([O:11][C:10]3[C:12]4[C:17]([C:18](=[O:21])[C:19](=[O:20])[C:9]=3[S:8][CH2:7]2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH2:5][CH2:4]1.Cl[C:25]([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=1)=[O:26].Cl>C(N(CC)CC)C>[O:20]=[C:19]1[C:9]2[S:8][CH2:7][C:6]3([CH2:22][CH2:23][CH:3]([NH:2][C:25](=[O:26])[O:27][C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:35])([F:37])[F:36])[CH:29]=4)[CH2:4][CH2:5]3)[O:11][C:10]=2[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]1=[O:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 50574253-(Trifluoromethyl)phenyl chloroformateHCID 674389234-Aminospiro[cyclohexane-1,2'-naphtho[1,2-b][1,4]oxathiine]-5',6'-dione hydrochloride

Product 1

HCID 576618523-(Trifluoromethyl)phenyl (5',6'-dioxo-5',6'-dihydrospiro[cyclohexane-1,2'-naphtho[1,2-b][1,4]oxathiin]-4-yl)carbamate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Compound 108 was synthesized using 4-aminospiro[cyclohexane-1,2′-naphtho[1,2-b][1,4]oxathiine]-5′,6′-dione hydrochloride, 3-(trifluoromethyl)phenyl chloroformate, triethyl amine to neutralize the hydrochloride and conditions outlined in procedure S. M.p.=198-199° C.; 400 MHz 1H NMR (DMSO-d6) δ: 8.08 (d, J=7.8 Hz, 1H), 7.92 (d, J=7.4 Hz, 1H), 7.83 (t, J=7.1 Hz, 1H), 7.78 (t, J=7.1 Hz, 1H), 7.66-7.43 (m, 4H), 3.56-3.47 (m, 1H), 3.04 (s, 2H), 2.16-2.05 (m, 2H), 1.94-1.80 (m, 2H), 1.78-1.66 (m, 7H), LCMS: 504 [M+H].

Sources & evidence

ORD record
ord-872df1ab09524931ab8c21621c3cb1c5
Source dataset
uspto-grants-2011_10
Patent number
US08039503B2

Reaction notes

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