HCID 131719937, compound → HCID 131719936, compound

HRID 977191Notes

Reaction equation

HRID 977191 reaction equation
[NH:1]([C:64]([O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:65])[C@H:2]([C:7]([NH:9][C@@H:10]([C:21]([NH:23][C@@H:24]([C:26]([NH:28][CH2:29][CH2:30][C:31]([NH:33][C@H:34]([C:43]([NH:45][C@@H:46]([C:54]([O:56]CC1C=CC=CC=1)=[O:55])[CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:44])[CH2:35][C:36]1[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=1)=[O:32])=[O:27])[CH3:25])=[O:22])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[H][H]>CO.[Pd]>[NH:1]([C:64]([O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:65])[C@H:2]([C:7]([NH:9][C@@H:10]([C:21]([NH:23][C@@H:24]([C:26]([NH:28][CH2:29][CH2:30][C:31]([NH:33][C@H:34]([C:43]([NH:45][C@@H:46]([C:54]([OH:56])=[O:55])[CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:44])[CH2:35][C:36]1[CH:37]=[CH:38][C:39]([OH:42])=[CH:40][CH:41]=1)=[O:32])=[O:27])[CH3:25])=[O:22])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

5

Reactant 2

HCID 131719937HCID 131719937, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131719936HCID 131719936, compoundYield 93.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Boc-Leu-(D)Trp-(D)Ala-βAla-Tyr-(D)Phe-OBzl (0.2 g) was dissolved in methanol (50 ml) and then catalytically reduced in a hydrogen stream in the presence of palladium black catalyst. After the catalyst was filtered out and the solvent was distilled off, the residue was dissolved in a 50% aqueous solution of acetic acid (3 ml) and applied to a column (2×95 cm) of Sephadex G-25, packed with 50% aqueous acetic acid, and developed with the same solvent. The major fractions were collected and lyophilized to yield a white powder of Boc-Leu-(D)Trp-(D)Ala-βAla-Tyr-(D)Phe-OH (170 mg).

Workup

  1. filtrationAfter the catalyst was filtered out
  2. distillationthe solvent was distilled off
  3. dissolutionthe residue was dissolved in a 50% aqueous solution of acetic acid (3 ml)
  4. customThe major fractions were collected

Sources & evidence

ORD record
ord-90f0395145ab4146a3be9bb195157c88
Source dataset
uspto-grants-1997_03
Patent number
US05614497

Reaction notes

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