HCID 131717779, compound → HCID 131717778, compound

HRID 2082234Notes

Reaction equation

HRID 2082234 reaction equation
[NH:1]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C@H:2]([C:13]([NH:15][C@@H:16]([C:29]([NH:31][C@H:32]([C:40]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:41])[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:30])[CH2:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]([CH:27]=[O:28])[CH:19]=1)=[O:14])[CH2:3][CH2:4][C:5](=[O:12])[O:6]CC(Cl)(Cl)Cl>CC(O)=O.[Zn]>[NH:1]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C@H:2]([C:13]([NH:15][C@@H:16]([C:29]([NH:31][C@H:32]([C:40]([O:42][CH2:43][C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)=[O:41])[CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)=[O:30])[CH2:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]([CH:27]=[O:28])[CH:19]=1)=[O:14])[CH2:3][CH2:4][C:5](=[O:6])[OH:12]

Participants

4

Reactant 1

HCID 131717779HCID 131717779, compound

Product 1

HCID 131717778HCID 131717778, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of Boc-Glu(OTce)-D-Trp(CHO)-Phe-OBzl (0.40 g) in 90% AcOH (10 ml), was added zinc (0.20 g). The mixture was stirred for four and half an hour at room temperature. After filtration and evaporation, the residue was extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride, and dried over magnesium sulfate. The evaporated residue was subjected to column chromatography on silica gel (20 g) and eluted with a mixture of chloroform and methanol (30:1 to 9:1, gradient elution). The fractions containing the object compound were combined and evaporated. The residue was pulverized with n-hexane, filtered and dried to give Boc-Glu-D-Trp(CHO)-Phe-OBzl (0.27 g).

Workup

  1. filtrationAfter filtration and evaporation
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. washeluted with a mixture of chloroform and methanol (30:1 to 9:1, gradient elution)
  6. additionThe fractions containing the object compound
  7. customevaporated
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-dcd9cf753e3d420896489b700be357b3
Source dataset
uspto-grants-1993_02
Patent number
US05187156

Reaction notes

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