Nitrogen → [2-(2-dihydroxymethyl-oxazol-4-ylmethyl)-2H-[1,2,3]triazol-4-yl]-carbamic acid 2-chloro-benzyl ester

HRID 42872Notes

Reaction equation

HRID 42872 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:14]=[N:13][N:12]([CH2:15][C:16]2[N:17]=[C:18]([CH2:21][OH:22])[O:19][CH:20]=2)[N:11]=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:14]=[N:13][N:12]([CH2:15][C:16]2[N:17]=[C:18]([CH:21]([OH:29])[OH:22])[O:19][CH:20]=2)[N:11]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 694302-OxopropiononitrileHCID 67364324[2-(2-Hydroxymethyl-oxazol-4-ylmethyl)-2H-[1,2,3]triazol-4-yl]-carbamic acid 2-chloro-benzyl ester

Product 1

HCID 67365246[2-(2-dihydroxymethyl-oxazol-4-ylmethyl)-2H-[1,2,3]triazol-4-yl]-carbamic acid 2-chloro-benzyl ester

Reagents, catalysts & solvents 1

HCID 14801Manganese dioxideCatalyst

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [2-(2-hydroxymethyl-oxazol-4-ylmethyl)-2H-[1,2,3]triazol-4-yl]-carbamic acid 2-chloro-benzyl ester (37 mg, 0.10 mmol) in AcCN (3.0 mL) was treated at rt with MnO2 (49 mg, 0.51 mmol) and the reaction mixture was stirred at rt for 16 h before being filtered through Celite. The solvent was removed under reduced pressure to give the title compound as a brown solid. TLC: rf (EA)=0.48. LC-MS-conditions 02: tR=0.83 min; [M+H]+=380.69.

Workup

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

Sources & evidence

ORD record
ord-9afd8c0694ef4be3984c234fc056e9eb
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Reaction notes

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