tert.-butoxycarbonyl-L-tyrosyl-D-phenylalanyl-glycine benzyl ester → tert.-butoxycarbonyl-L-tyrosyl-D-phenylalanyl-glycine

HRID 1759191Notes

Reaction equation

HRID 1759191 reaction equation
C([O:8][C:9](=[O:42])[CH2:10][NH:11][C:12](=[O:41])[C@@H:13]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[NH:14][C:15](=[O:33])[C@H:16]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)[NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])C1C=CC=CC=1>CO.[Pd]>[C:21]([O:20][C:18]([NH:17][C@H:16]([C:15]([NH:14][C@@H:13]([C:12]([NH:11][CH2:10][C:9]([OH:42])=[O:8])=[O:41])[CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:33])[CH2:25][C:26]1[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

4

Reactant 1

HCID 57281973tert.-butoxycarbonyl-L-tyrosyl-D-phenylalanyl-glycine benzyl ester

Product 1

HCID 57232727tert.-butoxycarbonyl-L-tyrosyl-D-phenylalanyl-glycineYield 89.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

23.0 g (40 mmoles) of the protected tripeptide ester obtained in Step 2 above are dissolved in 40 ml of methanol, and the mixture is hydrogenated in the presence of palladium-on-carbon catalyst. At the end of the reaction the catalyst is filtered off, washed with methanol, the filtrate and the wash are combined and evaporated under reduced pressure. The residue is triturated with diethyl ether, the solid is filtered off, washed with diethyl ether and dried in a vacuum desiccator. 17.45 g (89.8%) of tert.-butoxycarbonyl-L-tyrosyl-D-phenylalanyl-glycine are obtained; m.p.: 105°-110° C., Rf13 =0.2-0.3.

Workup

  1. customAt the end of the reaction the catalyst
  2. filtrationis filtered off
  3. washwashed with methanol
  4. customevaporated under reduced pressure
  5. customThe residue is triturated with diethyl ether
  6. filtrationthe solid is filtered off
  7. washwashed with diethyl ether
  8. customdried in a vacuum desiccator

Sources & evidence

ORD record
ord-833d405a33224c708f23ff5161ee782c
Source dataset
uspto-grants-1982_07
Patent number
US04339440

Reaction notes

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