Hydrochloric Acid → Hydrochloric Acid

HRID 527758Notes

Reaction equation

HRID 527758 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([N:10]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([O:36][CH3:37])=[O:35])=[CH:30][CH:29]=1)[C:11]([C@H:13]1[N:17](C(OC(C)(C)C)=O)[CH2:16][Si:15]([CH3:26])([CH3:25])[CH2:14]1)=[O:12])[CH3:9].[ClH:38]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([N:10]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([O:36][CH3:37])=[O:35])=[CH:30][CH:29]=1)[C:11]([C@H:13]1[NH:17][CH2:16][Si:15]([CH3:25])([CH3:26])[CH2:14]1)=[O:12])[CH3:9].[ClH:38]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 89930808HCID 89930808, compound

Product 2

HCID 313Hydrochloric AcidYield 1,268.5%HCID 89923793HCID 89923793, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-tert-butyl 5-(((R)-1-(2-fluorophenyl)ethyl)(4-(methoxycarbonyl)benzyl)carbamoyl)-3,3-dimethyl-1,3-azasilolidine-1-carboxylate (85 mg, 0.16 mmol) in DCM (4 mL) was added HCl (4.0 M solution in dioxane, 1.5 mL, 6.0 mmol). The resulting reaction mixture was stirred at rt for 1 h and concentrated in vacuo to give the title compound as a HCl salt (74 mg, 99%, white solid). 1H NMR (DMSO-d6) δ 7.92-7.74 (m, 1H), 7.68 (d, J=8.1 Hz, 1H), 7.60-7.41 (m, 1H), 7.35-7.06 (m, 3H), 7.03 (d, J=8.4 Hz, 1H), 6.96-6.75 (m, 1H), 5.71-5.43 (m, 1H), 4.85-4.41 (m, 2H), 4.37-4.12 (m, 1H), 3.88-3.77 (m, 3H), 3.73-3.48 (m, 1H), 2.70-2.54 (m, 1H), 2.34-2.13 (m, 1H), 1.73-1.56 (m, 2.5H), 1.47 (d, J=7.0 Hz, 0.5H), 1.39-1.17 (m, 1H), 1.00-0.63 (m, 1H), 0.45-0.17 (m, 6H); MS(ESI+) m/z 429.8 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-897b0c5deb4241ad914457ea8d70da78
Source dataset
uspto-grants-2016_05
Patent number
US09345740B2

Reaction notes

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