HCID 15600423, compound → HCID 54240983, compound

HRID 1111650Notes

Reaction equation

HRID 1111650 reaction equation
[CH3:1][O:2][C:3](=[O:38])[C@H:4]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[NH:5][C:6](=[O:30])[C@H:7]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[NH:8][C:9](=[O:22])[CH2:10][NH:11]C(OCC1C=CC=CC=1)=O>[Pd].C(O)(=O)C>[CH3:1][O:2][C:3](=[O:38])[C@H:4]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[NH:5][C:6](=[O:30])[C@H:7]([CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[NH:8][C:9](=[O:22])[CH2:10][NH2:11]

Participants

4

Reactant 1

HCID 15600423HCID 15600423, compound

Product 1

HCID 54240983HCID 54240983, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of benzyloxycarbonyl-glycyl-phenylalanyl-phenylalanine methyl ester (1.5 g, 2.9 mmoles described in Example 1) and 5% palladium on carbon (0.15 g) in acetic acid 140 ml) is rapidly stirred under an atmosphere of hydrogen until the benzyloxycarbonyl group is removed. The mixture is filtered and the filtrate is evaporated. The residue is triturated with ether to give a precipitate of glycyl-phenylalanyl-phenylalanine methyl ester. A solution of benzyloxycarbonly-(N6 -t-butoxycarbonyl)-lysine p-nitrophenyl ester [1.36 g, 2.7 mmoles, described by E. Sandrin and R. A. Boissonas, Helv. Chem. Acta. 46, 1637 (1963)] in dimethylformamide (20 ml) is added dropwise to a cooled solution of the above compound (1.2 g, 217 mmoles) and N-ethylmorpholine (1.35 ml, 2.7 mmoles). The reaction mixture is stirred overnight at room temperature and evaporated. The residue is dissolved in methanol (4 ml) and diethyl ether is added. The precipitate is crystallized from ethyl acetate-petroleum ether (30°-60° C.) to obtain the title compound, mp 139°-142° C.

Workup

  1. customis removed
  2. filtrationThe mixture is filtered
  3. customthe filtrate is evaporated
  4. customThe residue is triturated with ether

Sources & evidence

ORD record
ord-9d3209169baf4a7186c971d0948da392
Source dataset
uspto-grants-1978_10
Patent number
US04118380

Reaction notes

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