1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → tert-butyl (6R,7R)-6-carbamoyl-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

HRID 1022718Notes

Reaction equation

HRID 1022718 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][C@@H:13]([C:15](O)=[O:16])[C@H:12]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)[O:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH4+].[N:27]1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[C:15]([C@H:13]1[C@H:12]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)[O:11][CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:14]1)(=[O:16])[NH2:27]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220338091-Hydroxybenzotriazole, ammonium saltHCID 66975341(6R,7R)-4-(tert-butoxycarbonyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-6-carboxylic acid

Product 1

HCID 66976321tert-butyl (6R,7R)-6-carbamoyl-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylateYield 97.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (6R,7R)-4-(tert-butoxycarbonyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-6-carboxylic acid (450 mg) and 1H-benzotriazol-1-ol ammonium salt (211 mg) in DMF (5.8 mL) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (265 mg), and the mixture was stirred overnight. To the reaction mixture was added distilled water, and the mixture was extracted with ethyl acetate. The extract was washed with distilled water and brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (437 mg).

Workup

  1. additionTo the reaction mixture was added
  2. distillationdistilled water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with distilled water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-523157fd2ae441d8935ee2323d887d7e
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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