Guanidine Hydrochloride → HCID 178453694, compound

HRID 1699402Notes

Reaction equation

HRID 1699402 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[C:24]2[O:23][CH2:22][CH2:21][C:20]([C:25](OC)=[O:26])=[CH:19][C:18]=2[CH:17]=[CH:16][CH:15]=1)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:30][C:31]([NH2:33])=[NH:32].C[O-].[Na+].C(OCC)(=O)C>CN(C)C=O.CO.O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[C:24]2[O:23][CH2:22][CH2:21][C:20]([C:25]([NH:32][C:31]([NH2:33])=[NH:30])=[O:26])=[CH:19][C:18]=2[CH:17]=[CH:16][CH:15]=1)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 18319573HCID 18319573, compound

Product 1

HCID 178453694HCID 178453694, compoundYield 76.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of methyl 2,3-dihydro-9-[2-(tert-butoxycarbonylamino)ethylaminocarbonyl]-1-benzoxepin-4-carboxylate (1.1 g) and guanidine hydrochloride (1.3 g) in N,N-dimethylformamide (11 ml) was added 28% sodium methoxide in methanol (2.6 ml). The reaction mixture was stirred for 8 hours at ambient temperature, and the mixture was poured into a mixture of ethyl acetate and water. The separated organic layer was washed with water, dried over magnesium sulfate and evaporated in vacuo to give {2,3-dihydro-9-[2-(tert-butoxycarbonylamino)ethylaminocarbonyl]-1-benzoxepin-4-carbonyl}guanidine (0.9 g) as an oil.

Workup

  1. washThe separated organic layer was washed with water
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-47f682fdfc0c42e999ad3a31ec5fb7dc
Source dataset
uspto-grants-2002_02
Patent number
US06346527B1

Reaction notes

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