Ethyl hexanimidate hydrochloride → [(R)-1-Hydroxymethyl-1-methyl-3-(2-pentyl-benzoxazol-5-yl)-propyl]-carbamic acid tert-butyl ester

HRID 1170408Notes

Reaction equation

HRID 1170408 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C@:8]([CH2:20][OH:21])([CH3:19])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([NH2:18])[CH:12]=1)([CH3:4])([CH3:3])[CH3:2].Cl.C(O[C:27](=N)[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])C>C(Cl)Cl>[C:1]([O:5][C:6](=[O:22])[NH:7][C@:8]([CH2:20][OH:21])([CH3:19])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]2[O:17][C:27]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[N:18][C:13]=2[CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 18950931Ethyl hexanimidate hydrochlorideHCID 68768961[(R)-3-(3-Amino-4-hydroxy-phenyl)-1-hydroxymethyl-1-methyl-propyl]-carbamic acid tert-butyl ester

Product 1

HCID 68767645[(R)-1-Hydroxymethyl-1-methyl-3-(2-pentyl-benzoxazol-5-yl)-propyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [(R)-3-(3-Amino-4-hydroxy-phenyl)-1-hydroxymethyl-1-methyl-propyl]-carbamic acid tert-butyl ester (500 mg, 1.61 mmol) and hexanimidic acid ethyl ester hydrochloride (318 mg, 1.77 mmol) in DCM (6 ml) was stirred for 16 hours at RT. Evaporation of the solvent in vacuum was followed by silica gel chromatography (eluent: DCM/methanol 40/1). Product containing fractions were pooled and evaporated in vacuum. Crystallization from pentane provided the title compound as a colorless solid. mp: 92.7/92.6

Workup

  1. customEvaporation of the solvent in vacuum
  2. additionProduct containing fractions
  3. customevaporated in vacuum
  4. customCrystallization from pentane

Sources & evidence

ORD record
ord-6f925c27c6094caaa698a7e2f5738894
Source dataset
uspto-grants-2010_11
Patent number
US07825260B2

Reaction notes

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