Dimethylformamide → HCID 178479439, compound

HRID 1388176Notes

Reaction equation

HRID 1388176 reaction equation
CN(C)C=O.Cl.[NH:7]([CH2:11][CH2:12][CH2:13][CH2:14][C@H:15]([OH:20])[CH2:16][C:17]([NH2:19])=[O:18])[C:8]([NH2:10])=[NH:9].[C:21]([Cl:29])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>N1C=CC=CC=1>[ClH:29].[NH:7]([CH2:11][CH2:12][CH2:13][CH2:14][C@H:15]([O:20][C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:16][C:17]([NH2:19])=[O:18])[C:8]([NH2:10])=[NH:9]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7412Benzoyl chlorideHCID 178479440HCID 178479440, compound

Product 1

HCID 178479439HCID 178479439, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Into 2.5 ml of dimethylformamide, was dissolved 2.09 of (S)-7-guanidino-3-hydroxyheptanamide hydrochloride followed by 1.7 ml of pyridine. To the solution, while being cooled in ice, was added slowly and dropwise 2.6 ml of benzoyl chloride. The mixture was stirred for 30 minutes while cooling in ice and for further two hours at room temperature. The reaction mixture was diluted with 20 ml of ice water, the separated oily layer was separated, and the aqueous layer was admixed with 600 mg of sodium chloride. The aqueous layer was passed through a column of Diaion® HP-20 which had been equilibrated with 0.5 M aqueous sodium chloride solution, and the column was washed successively with 0.5 M, 0.2 M and 0.1 M aqueous sodium chloride solutions, and with water. The fractions eluted with 20 to 40% (v/v) aqueous methanol were collected and concentrated under reduced pressure to yield 820 mg of (S)-7-guanidino-3-benzoyloxyheptanamide hydrochloride in oily form. NMR: 1.4-2.0 (CH2 x3), 2.65 (CH2), 3.17 (CH2), 5.50 (CH), 7.2-8.1 (COC6H5).

Workup

  1. temperatureTo the solution, while being cooled in ice
  2. additionwas added slowly
  3. customthe separated oily layer was separated
  4. washthe column was washed successively with 0.5 M, 0.2 M and 0.1 M aqueous sodium chloride solutions
  5. washThe fractions eluted with 20 to 40% (v/v) aqueous methanol
  6. customwere collected
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fc4e005bb0a2405783e67cd3f456641d
Source dataset
uspto-grants-1984_02
Patent number
US04430346

Reaction notes

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