Hydrogen Bromide → HCID 46937588, compound

HRID 1963500Notes

Reaction equation

HRID 1963500 reaction equation
[CH3:1][N:2]1[N:6]=[N:5][C:4]([C@H:7]2[CH2:12][C@@H:11]([C:13]3[O:17][NH:16][C:15](=[O:18])[CH:14]=3)[CH2:10][CH2:9][N:8]2C(OCC2C=CC=CC=2)=O)=[N:3]1.Br>>[CH3:1][N:2]1[N:6]=[N:5][C:4]([C@H:7]2[CH2:12][C@@H:11]([C:13]3[O:17][NH:16][C:15](=[O:18])[CH:14]=3)[CH2:10][CH2:9][NH:8]2)=[N:3]1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 86646613HCID 86646613, compound

Product 1

HCID 46937588HCID 46937588, compoundYield 73.3%

Procedure

(2R,4S)-Benzyl 2-(2-methyl-2H-tetrazol-5-yl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (301 mg, 0.78 mmol) was dissolved in hydrogen bromide (33% in AcOH) (4.1 mL, 23.49 mmol) and reacted for 1 h. The mixture was evaporated and the residue was partitioned between water and EtOAc. The aqueous phase was purified by preparative HPLC on a Kromasil C8 column (10 μm 250×50 ID mm) using a gradient of 0-15% Acetonitrile in H2O/MeCN/NH3 95/5/0.2 buffer over 20 minutes with a flow of 100 mL/min. 5-((2R,4S)-2-(2-Methyl-2H-tetrazol-5-yl)piperidin-4-yl)isoxazol-3(2H)-one (143 mg, 73%) was isolated. 1H NMR (400 MHz, cdcl3) δ 1.70 (qd, 1H), 1.85 (q, 1H), 2.04-2.12 (m, 1H), 2.43-2.50 (m, 1H), 2.91-3.02 (m, 2H), 3.33-3.41 (m, 1H), 4.18 (dd, 1H), 4.32 (s, 3H), 5.68 (s, 1H). HRMS Calcd for [C10H14N6O2+H]+: 251.1256. Found: 251.1233.

Workup

  1. customreacted for 1 h
  2. customThe mixture was evaporated
  3. customthe residue was partitioned between water and EtOAc
  4. customThe aqueous phase was purified by preparative HPLC on a Kromasil C8 column (10 μm 250×50 ID mm)
  5. custombuffer over 20 minutes

Sources & evidence

ORD record
ord-88c6eed7443542558c2b89a32bbf3805
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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