Hydrogen Bromide → HCID 178513920, compound

HRID 1252526Notes

Reaction equation

HRID 1252526 reaction equation
Br.C(OC([NH:12][C@@H:13]([CH2:33][C:34](=[O:53])[NH:35]C(C1C=CC(OC)=CC=1)C1C=CC(OC)=CC=1)[C:14]([NH:16][C@@H:17]([CH2:21][NH:22][C@H:23]([C:30]([OH:32])=[O:31])[CH2:24][C:25]1[N:26]=[CH:27][NH:28][CH:29]=1)[C:18]([OH:20])=[O:19])=[O:15])=O)C1C=CC=CC=1.C(OCC)(=O)C>C(O)(=O)C>[NH2:12][C@@H:13]([CH2:33][C:34](=[O:53])[NH2:35])[C:14]([NH:16][C@@H:17]([CH2:21][NH:22][C@H:23]([C:30]([OH:32])=[O:31])[CH2:24][C:25]1[N:26]=[CH:27][NH:28][CH:29]=1)[C:18]([OH:20])=[O:19])=[O:15]

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 8857Ethyl AcetateHCID 178491196HCID 178491196, compound

Product 1

HCID 178513920HCID 178513920, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 30% hydrogen bromide in acetic acid (4.0 ml) was added to (2S)-2-[[(2S)-2-benzyloxycarbonylamino-3-[N-[bis(4-methoxyphenyl)methyl]carbamoyl]propionyl]amino]-3-[[(1S)-1-carboxy-2-(4-imidazolyl)ethyl]amino]propionic acid (772 mg) in an ice-water bath. The mixture was stirred for 15 minutes and then additional portion (4.0 ml) of a solution of hydrogen bromide in acetic acid was added thereto at ambient temperature. The mixture was stirred for 2.5 hours, and poured into a mixture of ice-water (25 ml) and ethyl acetate (25 ml). The aqueous layer was separated and then the remaining organic layer was extracted with water (30 ml). The aqueous layer were combined and subjected to a column of Dowex 50W x 8 (H30 , 20 ml) and the elution was carried out with water (200 ml) and 1.4% aqueous ammonia (250 ml). The fractions containing the object compound were combined and evaporated in vacuo. The residue was dissolved in water (30 ml) and filtered. The filtrate was lyophilized to give a white powder (315 mg) of (2S)-2-[[(2S)-2-amino-3-carbamoylpropionyl]amino]-3-[[(1S)-1-carboxy-2-(4-imidazolyl)ethyl]amino]propionic acid.

Workup

  1. customat ambient temperature
  2. stirringThe mixture was stirred for 2.5 hours
  3. customThe aqueous layer was separated
  4. extractionthe remaining organic layer was extracted with water (30 ml)
  5. washthe elution
  6. additionThe fractions containing the object compound
  7. customevaporated in vacuo
  8. dissolutionThe residue was dissolved in water (30 ml)
  9. filtrationfiltered

Sources & evidence

ORD record
ord-981ee392a28347d3b92f976ef15c5b8d
Source dataset
uspto-grants-1988_05
Patent number
US04743614

Reaction notes

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