Nitrogen → [1-(2-dihydroxymethyl-oxazol-4-ylmethyl)-1H-pyrazol-4-yl]-carbamic acid 2-chloro-benzyl ester

HRID 2065090Notes

Reaction equation

N#N.[Cl:3][C:4]1[CH:27]=[CH:26][CH:25]=[CH:24][C:5]=1[CH2:6][O:7][C:8](=[O:23])[NH:9][C:10]1[CH:11]=[N:12][N:13]([CH2:15][C:16]2[N:17]=[C:18]([CH2:21][OH:22])[O:19][CH:20]=2)[CH:14]=1.C(C#N)(C)=[O:29]>O=[Mn]=O>[Cl:3][C:4]1[CH:27]=[CH:26][CH:25]=[CH:24][C:5]=1[CH2:6][O:7][C:8](=[O:23])[NH:9][C:10]1[CH:11]=[N:12][N:13]([CH2:15][C:16]2[N:17]=[C:18]([CH:21]([OH:29])[OH:22])[O:19][CH:20]=2)[CH:14]=1

Participants

Conditions

Temperature: 55 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [1-(2-hydroxymethyl-oxazol-4-ylmethyl)-1H-pyrazol-4-yl]-carbamic acid 2-chloro-benzyl ester (238 mg, 0.65 mmol) in AcCN (5.0 mL) was treated at rt with MnO2 (317 mg, 3.28 mmol) and the reaction mixture was stirred at 55° C. for 4 h before being filtered through Celite. The solvent was removed under reduced pressure to give the title compound as a brown oil. TLC: rf (EA)=0.48. LC-MS-conditions 02: tR=0.81 min; [M+H]+=379.22.

Workup

filtrationbefore being filtered through Celite
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-fcabd32b291541868f156c6b8a96af1e
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288419B2

Reaction notes

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