Einecs 211-027-4 → HCID 178454168, compound

HRID 2082227Notes

Reaction equation

HRID 2082227 reaction equation
[NH:1]([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[C@H:2]([C:19]([NH:21][C@@H:22]([C:35]([NH:37][C@H:38]([C:46]([O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:47])[CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:36])[CH2:23][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:26]([CH:33]=[O:34])[CH:25]=1)=[O:20])[CH2:3][C:4]1[N:8]=[CH:7][N:6](S(C2C=CC(C)=CC=2)(=O)=O)[CH:5]=1.[Cl-].[NH+]1C=CC=CC=1>CN(C=O)C>[NH:1]([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[C@H:2]([C:19]([NH:21][C@@H:22]([C:35]([NH:37][C@H:38]([C:46]([O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:47])[CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)=[O:36])[CH2:23][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:26]([CH:33]=[O:34])[CH:25]=1)=[O:20])[CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1

Participants

4

Reactant 2

HCID 69401Einecs 211-027-42×HCID 131717768HCID 131717768, compound

Product 1

HCID 178454168HCID 178454168, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Boc-His(Tos)-D-Trp(CHO)-Phe-OBzl (1.16 g) in DMF (35 ml) was added pyridinium chloride (1.6 g) at room temperature. After stirring for one and half an hour, additional pyridinium chloride (0.4 g) was added and the mixture was stirred for additional 50 minutes. After evaporation, the residue was solidified with water, filtered, washed with 2% hydrochloric acid, water, 2% sodium hydrogencarbonate, water, and dried. The powder was subjected to column chromatography on silica gel (100 g) and eluted with a mixture of chloroform and methanol (20:1). The fractions containing the object compound were combined and evaporated. The residue was dissolved in ethanol and reprecipitated with water, filtered and dried to give Boc-His-D-Trp(CHO)-Phe-OBzl (0.70 g).

Workup

  1. additionwas added
  2. customAfter evaporation
  3. filtrationfiltered
  4. washwashed with 2% hydrochloric acid, water, 2% sodium hydrogencarbonate, water
  5. customdried
  6. washeluted with a mixture of chloroform and methanol (20:1)
  7. additionThe fractions containing the object compound
  8. customevaporated
  9. dissolutionThe residue was dissolved in ethanol
  10. customreprecipitated with water
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-bf0ffe3beb07470d9d5f40b9465dd1b3
Source dataset
uspto-grants-1993_02
Patent number
US05187156

Reaction notes

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