1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl (6SR,7SR)-6-(3,4-dichlorophenyl)-7-{[(1H-1,2,4-triazol-1-ylacetyl)amino]methyl}-1,4-oxazepane-4-carboxylate

HRID 1022814Notes

Reaction equation

HRID 1022814 reaction equation
[NH2:1][CH2:2][CH:3]1[O:9][CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5][CH:4]1[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[N:46]1([CH2:51][C:52](O)=[O:53])[CH:50]=[N:49][CH:48]=[N:47]1.C(=O)([O-])O.[Na+]>CN(C=O)C.C(N(CC)CC)C>[Cl:24][C:19]1[CH:18]=[C:17]([CH:4]2[CH:3]([CH2:2][NH:1][C:52](=[O:53])[CH2:51][N:46]3[CH:50]=[N:49][CH:48]=[N:47]3)[O:9][CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]2)[CH:22]=[CH:21][C:20]=1[Cl:23]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 18101801,2,4-Triazole-1-acetic acidHCID 66975190tert-butyl (6RS,7SR)-7-(aminomethyl)-6-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

Product 1

HCID 66976357tert-butyl (6SR,7SR)-6-(3,4-dichlorophenyl)-7-{[(1H-1,2,4-triazol-1-ylacetyl)amino]methyl}-1,4-oxazepane-4-carboxylateYield 73.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of tert-butyl (6SR,7SR)-7-(aminomethyl)-6-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (200 mg) in DMF (5 mL) were added WSC (100 mg), HOBt (90 mg), triethylamine (0.10 mL) and 2-(1H-1,2,4-triazol-1-yl)acetic acid (74 mg), and the mixture was stirred at room temperature overnight. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (190 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1f6867cb3bf64e0ea833723f471d5ac2
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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