1-Hydroxybenzotriazole → (R)-tert-butyl 4-(methoxy(methyl)amino)-4-oxobutan-2-ylcarbamate

HRID 854272Notes

Reaction equation

HRID 854272 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH3:14])[CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.Cl.[CH3:38][NH:39][O:40][CH3:41]>C(#N)C.C(N(CC)CC)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([CH3:14])[CH2:10][C:11]([N:39]([O:40][CH3:41])[CH3:38])=[O:13])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2761507(R)-3-((tert-butoxycarbonyl)amino)butanoic acid

Product 1

HCID 25139072(R)-tert-butyl 4-(methoxy(methyl)amino)-4-oxobutan-2-ylcarbamate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

A solution of (3R)-3-[(tert-butoxycarbonyl)amino]butanoic acid (1 g, 5 mmol) in acetonitrile (40 mL) was treated with 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC; 1.05 g, 5.5 mmol), 1-hydroxybenzotriazole (HOBt; 810 mg, 6 mmol), N,O-dimethylhydroxylamine hydrochloride (1.0 g, 10 mmol) and triethylamine (1.4 mL) and stirred at room temperature for 2 d. The solution was evaporated and the residue purified by flash chromatography on a Biotage® system (silica gel, 40-90% ethyl acetate/hexane gradient) to yield the desired product as a colorless viscous oil. MS 269.1 (M+Na).

Workup

  1. customThe solution was evaporated
  2. customthe residue purified by flash chromatography on a Biotage® system (silica gel, 40-90% ethyl acetate/hexane gradient)

Sources & evidence

ORD record
ord-16b3a8de8ce640e383c43107eeaa4935
Source dataset
uspto-grants-2007_08
Patent number
US07259160B2

Reaction notes

Loading…