HCID 131714385, compound → HCID 131714384, compound

HRID 464553Notes

Reaction equation

HRID 464553 reaction equation
[NH:1]([C:37]([O:39][CH2:40][CH:41]1[C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[C:47]2[C:42]1=[CH:43][CH:44]=[CH:45][CH:46]=2)=[O:38])[C@H:2]([C:15]([NH:17][C@H:18]([C:27]([O:29]CC1C=CC=CC=1)=[O:28])[CH2:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]>CN(C)C=O.[Pd]>[NH:1]([C:37]([O:39][CH2:40][CH:41]1[C:42]2[C:47](=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:48]2[C:53]1=[CH:52][CH:51]=[CH:50][CH:49]=2)=[O:38])[C@H:2]([C:15]([NH:17][C@H:18]([C:27]([OH:29])=[O:28])[CH2:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9]

Participants

4

Reactant 1

HCID 131714385HCID 131714385, compound

Product 1

HCID 131714384HCID 131714384, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of FMOC-Lys(Boc)-Asp(O-t-Bu)-OBzl (37) (5.0 g, 6.9 M) in dimethylformamide (50 ml) was added 10 percent Pd/C. (500 mg). The mixture was hydrogenated for 5 hrs at 50 psi H2. The solids were removed by filtration and the solvents removed under reduced pressure. This material was chromatographed on silica gel, eluting with acetone/methylene chloride/acetic acid 25/74/1 to give 4.3 g (98 percent) of 40 which was used without further characterization.

Workup

  1. customThe solids were removed by filtration
  2. customthe solvents removed under reduced pressure
  3. customThis material was chromatographed on silica gel
  4. washeluting with acetone/methylene chloride/acetic acid 25/74/1

Sources & evidence

ORD record
ord-e723bbea9b774814a88b806658e48770
Source dataset
uspto-grants-1985_10
Patent number
US04547489

Reaction notes

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