Acetonitrile → 2-(((Benzyloxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)propanoic acid

HRID 12403Notes

Reaction equation

HRID 12403 reaction equation
[CH2:1]([O:8][C:9]([NH:11]C(C(O)=O)CC(=O)N)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20](OCC)(=O)C.[C:26](#[N:28])C.[C:29]([OH:32])(=[O:31])[CH3:30].[C:33]([OH:36])(=[O:35])C.I([C:39]1[CH:44]=[CH:43]C=CC=1)=O>O>[CH2:1]([O:8][C:9]([NH:11][CH:30]([CH2:26][NH:28][C:33]([O:36][C:44]([CH3:43])([CH3:39])[CH3:20])=[O:35])[C:29]([OH:32])=[O:31])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 246565Carbobenzoxy-L-asparagineHCID 73357407Acetic acid;iodosylbenzene

Product 1

HCID 41154162-(((Benzyloxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)propanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To N-(benzyloxycarbonyl)-DL-asparagine (7.5 g) were added ethyl acetate (36 ml), acetonitrile (36 ml), water (18 ml) and iodosobenzene diacetate (10 g), and the mixture was stirred overnight at room temperature. The reaction mixture was filtered and, after washing the obtained solid with ethyl acetate, dioxane (180 ml), water (40 ml), 1N aqueous sodium hydroxide solution (10 ml) and di-t-butyl dicarbonate (6.1 g) were added, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate and washed with 0.5N hydrochloric acid. The solvent was evaporated to give 2-benzyloxycarbonylamino-3-tert-butoxycarbonylaminopropionic acid as a crude product. The crude product was treated in the same manner as in Step 1 of Example 15 to give (2-benzyloxycarbonylamino-3-hydroxypropyl)carbamic acid tert-butyl ester (2 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washafter washing the obtained solid with ethyl acetate, dioxane (180 ml), water (40 ml), 1N aqueous sodium hydroxide solution (10 ml) and di-t-butyl dicarbonate (6.1 g)
  3. additionwere added
  4. stirringthe mixture was stirred overnight at room temperature
  5. additionThe reaction mixture was diluted with ethyl acetate
  6. washwashed with 0.5N hydrochloric acid
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-090ebc008d494b28bcd771d148fefc56
Source dataset
uspto-grants-2010_06
Patent number
US07728005B2

Reaction notes

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