Acetic Anhydride → HCID 178475071, compound

HRID 1252530Notes

Reaction equation

HRID 1252530 reaction equation
[NH2:1][C@@H:2]([CH2:23][C:24](=[O:26])[NH2:25])[C:3]([NH:5][C@@H:6]([C@H:10]([NH:12][C@H:13]([C:20]([OH:22])=[O:21])[CH2:14][C:15]1[N:16]=[CH:17][NH:18][CH:19]=1)[CH3:11])[C:7]([OH:9])=[O:8])=[O:4].C(N(CC)CC)C.[C:34](OC(=O)C)(=[O:36])[CH3:35]>CO.O>[C:34]([NH:1][C@@H:2]([CH2:23][C:24](=[O:26])[NH2:25])[C:3]([NH:5][C@@H:6]([C@H:10]([NH:12][C@H:13]([C:20]([OH:22])=[O:21])[CH2:14][C:15]1[N:16]=[CH:17][NH:18][CH:19]=1)[CH3:11])[C:7]([OH:9])=[O:8])=[O:4])(=[O:36])[CH3:35]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 178462027HCID 178462027, compound

Product 1

HCID 178475071HCID 178475071, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of (2S, 3R)-2-[[(2S)-2-amino-3-carbamoylpropionyl] amino]-3-[[(1S)-1-carboxy-2-(4imidazolyl)ethyl]amino]butyric acid (500 mg) and triethylamine (0.38 ml) in a mixture of methanol(30 ml) and water (6 ml) was added acetic anhydride (0.13 ml) and the mixture was stirred for 20 hours at room temperature After removal of the solvent in vacuo, the residue was dissolved in water and adjusted to pH 3 with 1N hydrochloric acid. The solution was subjected to a column of Dowex 50W X 8 (H+ form, 10 ml) and the column was washed with water. The elution was carried out with 2% aqueous ammonia. The object fractions were collected and evaporated in vacuo and the residue was dissolved in a mixture of acetic acid (28.6 ml) and water (500 ml). The solution was lyophilized and the residue was solidified with methanol to give (2S, 3R)-2-[[(2S)-2-acetylamino-3-carbamoylpropionyl]amino]-3-[[(1S)-1 -carboxy-2-(4-imidazolyl)ethyl]amino]butyric acid (500 mg).

Workup

  1. customAfter removal of the solvent in vacuo
  2. dissolutionthe residue was dissolved in water
  3. washthe column was washed with water
  4. washThe elution
  5. customThe object fractions were collected
  6. customevaporated in vacuo
  7. dissolutionthe residue was dissolved in a mixture of acetic acid (28.6 ml) and water (500 ml)

Sources & evidence

ORD record
ord-9ab3e7a40a2344bd8ac79a9bb819c5ee
Source dataset
uspto-grants-1988_05
Patent number
US04743614

Reaction notes

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