1-Hydroxybenzotriazole → HCID 10637968, compound

HRID 440790Notes

Reaction equation

HRID 440790 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][CH2:15][C:14]([CH3:18])([CH3:17])[CH2:13][CH:9]1[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:19][N:20](Cl)[O:21][CH3:22].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)C.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[CH2:16][CH2:15][C:14]([CH3:18])([CH3:17])[CH2:13][CH:9]1[C:10]([N:20]([O:21][CH3:22])[CH3:19])=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 548183HCID 548183, compoundHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 105153011-(tert-butoxycarbonyl)-4,4-dimethylpiperidine-2-carboxylic acid

Product 1

HCID 10637968HCID 10637968, compoundYield 83.9%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 1-tert-butyloxycarbonyl-4,4-dimethylpipecolic acid (24.6 g), N,O-dimethylhydroxylamino hydrochloride (12.12 g) and 1-hydroxybenzotriazole (18.09 g) in anhydrous dimethylformamide (400 ml) was added anhydrous triethylamine (30.7 ml) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (21.08 g) and the resulting mixture was stirred at room temperature for 23 hours under a nitrogen atmosphere. Diethyl ether (1 l) was added and the mixture was washed with 1N hydrochloric acid (2×250 ml), 1N sodium hydroxide (1×250 ml), brine (1×200 ml), dried (MgSO4) and concentrated. Flash chromatography (silica gel, hexane-diethyl ether, 40:60) of the residue afforded the title compound (24.1 g) as a white solid; δH (250 MHz, CDCl3) 4.76 (1H, br s), 3.92-3.74 (1H, m), 3.75 (3H, s), 3.58-3.42 (1H, m), 3.19 (3H, s), 1.84 (1H, dd, J=14.0 and 3.3 Hz), 1.64 (1H, dd, J=14.0 and 7.6 Hz), 1.52-1.34 (11H, m and s), 0.94 (3H, s), 0.92 (3H, s); m/z (CI)301 (M+ +1).

Workup

  1. washthe mixture was washed with 1N hydrochloric acid (2×250 ml), 1N sodium hydroxide (1×250 ml), brine (1×200 ml)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b4de08a3eadc485fb60113af0ead9355
Source dataset
uspto-grants-1996_05
Patent number
US05521175

Reaction notes

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