Benzyloxycarbonyl-L-proline → HCID 178512875, compound

HRID 223314Notes

Reaction equation

HRID 223314 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:19][C@H:20]([C:28]([OH:30])=[O:29])[CH2:21][CH2:22][CH2:23][NH:24][C:25](=[NH:27])[NH2:26]>O1CCOCC1.O>[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([NH:19][C@H:20]([C:28]([OH:30])=[O:29])[CH2:21][CH2:22][CH2:23][NH:24][C:25](=[NH:26])[NH2:27])=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 101987Benzyloxycarbonyl-L-prolineHCID 178418600HCID 178418600, compound

Product 1

HCID 178512875HCID 178512875, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 37 g (0.1 mol) of p-nitrophenyl ester of benzyloxycarbonylproline in 360 ml of dioxane there is added a solution of 16 g (0.09 mol) of arginine in 160 ml of water under vigorous stirring. Two hours thereafter the solvent is evaporated and the precipitate is dissolved in 100 ml of dimethylformamide. The solution is stirred at room temperature for 72 hours and poured into 1 liter of ethylacetate. The resulting residue is filtered-off, washed on the filter with ethylacetate and reprecipitated from a mixture ethanol-ethylacetate. The yield of product (I) is 35 g (96%); the product has the following properties: M.p. 190° C., [α]D20 -46.6°; (c 1.0; H2O); Rf =0.53 (A, "Silufol") 0.66 (B, "Eastman"); EHis =0.56 (pH=2.4).

Workup

  1. customTwo hours thereafter the solvent is evaporated
  2. dissolutionthe precipitate is dissolved in 100 ml of dimethylformamide
  3. additionpoured into 1 liter of ethylacetate
  4. washwashed on the
  5. filtrationfilter with ethylacetate
  6. customreprecipitated from a mixture ethanol-ethylacetate

Sources & evidence

ORD record
ord-97641a96c18a471692c4d73a6ed2f98c
Source dataset
uspto-grants-1982_10
Patent number
US04353823

Reaction notes

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