HCID 178418361, compound → HCID 178427501, compound

HRID 2416128Notes

Reaction equation

HRID 2416128 reaction equation
[NH:1]1[C:64](=[O:65])[C@H:60]([CH:61]([CH3:63])[CH3:62])[N:59]([CH3:66])[C:57](=[O:58])[C@@H:49]([CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[NH:48][C:46](=[O:47])[C@H:34]([CH2:35][C:36](=[O:45])[O:37]CC2C=CC=CC=2)[NH:33][C:31](=[O:32])[CH2:30][NH:29][C:27](=[O:28])[C@@H:2]1[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:26])[NH:8][S:9]([C:12]1[C:24]([CH3:25])=[C:23]2[C:17]([O:18][C:19]([CH2:22]2)([CH3:21])[CH3:20])=[C:15]([CH3:16])[C:13]=1[CH3:14])(=[O:11])=[O:10].[H][H]>C1COCC1.[Pd]>[NH:1]1[C:64](=[O:65])[C@H:60]([CH:61]([CH3:63])[CH3:62])[N:59]([CH3:66])[C:57](=[O:58])[C@@H:49]([CH2:50][C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[NH:48][C:46](=[O:47])[C@H:34]([CH2:35][C:36](=[O:37])[OH:45])[NH:33][C:31](=[O:32])[CH2:30][NH:29][C:27](=[O:28])[C@@H:2]1[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:26])[NH:8][S:9]([C:12]1[C:24]([CH3:25])=[C:23]2[C:17]([O:18][C:19]([CH2:22]2)([CH3:20])[CH3:21])=[C:15]([CH3:16])[C:13]=1[CH3:14])(=[O:10])=[O:11]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178427500HCID 178427500, compound

Product 1

HCID 178427501HCID 178427501, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2 g of cyclo(Arg(Pbf)-Gly-Asp(OBzl)-DPhe-NMeVal) in 26 ml of THF is mixed with 0.5 g of Pd/C (10%). Hydrogen is passed through for 2 hours, the mixture is freed of the catalyst and the solvent is removed in vacuo. The product crystallizes after addition of 32 ml of acetone, and is filtered off and dried. Cyclo(Arg(Pbf)-Gly-Asp-DPhe-NMeVal) is obtained in a yield of 83%.

Workup

  1. customis passed through for 2 hours
  2. customthe solvent is removed in vacuo
  3. customThe product crystallizes
  4. additionafter addition of 32 ml of acetone
  5. filtrationis filtered off
  6. customdried

Sources & evidence

ORD record
ord-2f9bd696ad0b4429add31aa725d4efef
Source dataset
uspto-grants-2004_11
Patent number
US06822074B1

Reaction notes

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