4-Methylmorpholine → N-(t-butyloxy)-2-[[4-methoxybenzenesulfonyl](benzyl)amino]-2-[(2-methyl-5-tetrazolyl)methyl]acetamide

HRID 1720622Notes

Reaction equation

HRID 1720622 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:13]([CH2:17][C:18]2[N:19]=[N:20][N:21]([CH3:23])[N:22]=2)[C:14]([OH:16])=O)(=[O:11])=[O:10])=[CH:5][CH:4]=1.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.[C:49]([O:53][NH2:54])([CH3:52])([CH3:51])[CH3:50].Cl.CN(CCCN=C=NCC)C>C(Cl)Cl.O>[C:49]([O:53][NH:54][C:14](=[O:16])[CH:13]([N:12]([S:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)(=[O:11])=[O:10])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:17][C:18]1[N:19]=[N:20][N:21]([CH3:23])[N:22]=1)([CH3:52])([CH3:51])[CH3:50]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 228562822(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]-2-[(2-methyl-5-tetrazolyl)methyl]acetic acid

Product 1

HCID 22907048N-(t-butyloxy)-2-[[4-methoxybenzenesulfonyl](benzyl)amino]-2-[(2-methyl-5-tetrazolyl)methyl]acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]-2-[(2-methyl-5-tetrazolyl)methyl]acetic acid (0.96 g, 2.24 mmol), 1-hydroxybenzotriazole (0.30 g, 2.24 mmol), 4-methylmorpholine (0.86 mL, 7.89 mmol), and O-t-butylhydroxylamine hydrochloride (0.30 g, 2.24 mmol) are dissolved in methylene chloride (75.0 mL). N-[dimethylaminopropyl]-N'-ethylcarbodiimide hydrochloride (0.86 g, 4.48 mmol) is added, and the reaction is stirred overnight. The reaction is then diluted with water and extracted with methylene chloride. The combined organic extracts are washed with brine, dried (Na2SO4), and the solvent is evaporated. The crude product is purified by silica gel chromatography (50% ethyl acetate/hexane) to give N-(t-butyloxy)-2-[[4-methoxybenzenesulfonyl](benzyl)amino]-2-[(2-methyl-5-tetrazolyl)methyl]acetamide.

Workup

  1. extractionextracted with methylene chloride
  2. washThe combined organic extracts are washed with brine
  3. dry with materialdried (Na2SO4)
  4. customthe solvent is evaporated
  5. customThe crude product is purified by silica gel chromatography (50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-fbcab8208fda46d78924cad37f55ed9d
Source dataset
uspto-grants-1996_04
Patent number
US05506242

Reaction notes

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