Hydrochloric Acid → HCID 68999253, compound

HRID 750044Notes

Reaction equation

HRID 750044 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[O:23][C:24]3[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=3[N:26]=2)=[CH:17][CH:16]=1)=O)(C)(C)C.[ClH:31]>O1CCOCC1>[ClH:31].[O:23]1[C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=[C:22]1[O:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][C@H:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68999686HCID 68999686, compound

Product 1

HCID 68999253HCID 68999253, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 20 mL vial which contained a solution of (R)-2-[4-(benzooxazol-2-yloxy)-phenoxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (40 mg, 0.1 mmol) in dioxane (0.5 mL) was added HCl (4 N in dioxane 2 mL) at 0° C. The mixture was allowed to warm to rt and stir at rt for 16 h. Removal of the solvent yielded the title product (28 mg, 80%); LCMS; 75% ESI+, Calcd: 310.4. Found m/z: 311.4 (M+1). 1H NMR (400 MHz, DMSO-d6); δ 1.68-1.75 (m, 1H), 1.85-2.03 (m, 2H), 2.06-2.13 (m, 1H), 3.14-3.26 (m, 2H), 3.79-3.89 (m, 1H), 3.98-4.03 (m, 1H), 4.12 (dd, J/=10.4 Hz, J2=3.6 Hz, 1H), 6.69-6.72 (m, 2H), 6.78-6.83 (m, 2H), 7.05-7.16 (m, 3H), 7.25-7.30 (m, 1H).

Workup

  1. customRemoval of the solvent

Sources & evidence

ORD record
ord-46410070fbb840a0bf0ba1724b7174eb
Source dataset
uspto-grants-2008_07
Patent number
US07402684B2

Reaction notes

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