Hydrochloric Acid → HCID 131734229, compound

HRID 1498774Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:34]([F:37])([F:36])[F:35])[O:14][N:13]=[C:12]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[C:20]3([CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24]3)[O:19][CH2:18]4)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8].Cl>CO>[ClH:1].[Cl:9][C:6]1[CH:5]=[C:4]([C:10]2([C:34]([F:35])([F:37])[F:36])[O:14][N:13]=[C:12]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[C:20]3([CH2:24][NH:25][CH2:26]3)[O:19][CH2:18]4)[CH2:11]2)[CH:3]=[C:2]([Cl:1])[C:7]=1[F:8]

Participants

Conditions

Temperature: 65 °C

Procedure

Chiral-tert-butyl 5′-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-3′H-spiro[azetidine-3,1′-isobenzofuran]-1-carboxylate (Preparation 5, 1.1 g, 2.0 mmol) was dissolved in methanol (50 mL). A methanolic solution of HCl (5 mL of a 1.25M solution) was added and the reaction was heated to 65° C. for 18 hours. The reaction was cooled and concentrated under vacuum to afford the intermediate (980 mg, 100%) a solid. 1H NMR, 300 MHz (d6-DMSO) δ ppm: 9.86 (1H), 9.45 (1H), 8.14 (1H), 7.82 (3H), 7.70 (1H), 5.15 (2H), 4.41-4.30 (6H); m/z (CI) 461 [M+H] (free amine). The asterisk (*) depicts a chiral center.

Workup

temperatureThe reaction was cooled
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-b4f9dd42d3db45c5a0fa3a9441b78ded
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09200003B2

Reaction notes

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