Hydrochloric Acid → HCID 131717777, compound

HRID 2082233Notes

Reaction equation

HRID 2082233 reaction equation
Cl.[NH2:2][C@H:3]([C:9]([NH:11][C@@H:12]([C:25]([NH:27][C@H:28]([C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:26])[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]([CH:23]=[O:24])[CH:15]=1)=[O:10])[CH2:4][CH2:5][C:6](=[O:8])[NH2:7].[CH:46]([O-])=[O:47].[Na+].CC(OC(C)=O)=O>C(O)=O.O>[CH:46]([NH:2][C@H:3]([C:9]([NH:11][C@@H:12]([C:25]([NH:27][C@H:28]([C:36]([O:38][CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)=[O:37])[CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:26])[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]([CH:23]=[O:24])[CH:15]=1)=[O:10])[CH2:4][CH2:5][C:6](=[O:8])[NH2:7])=[O:47]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 2723810Sodium FormateHCID 44304144HCID 44304144, compound

Product 1

HCID 131717777HCID 131717777, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of HCl.H-Gln-D-Trp(CHO)-Phe-OBzl (0.33 g) and sodium formate (0.35 g) in formic acid (21 ml) was added dropwise Ac2O (7 ml) under ice-cooling. The mixture was stirred for three and half an hour at room temperature. Water (10 ml) was added to the mixture and then evaporated. To the residue, water was added and evaporated. The residue was pulverized with water, filtered. The solids were dissolved in DMF and reprecipitated with ethyl acetate, filtered and dried to give HCO-Gln-D-Trp(CHO)-Phe-OBzl (0.27 g).

Workup

  1. temperaturecooling
  2. customevaporated
  3. additionTo the residue, water was added
  4. customevaporated
  5. filtrationfiltered
  6. dissolutionThe solids were dissolved in DMF
  7. customreprecipitated with ethyl acetate
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-cf86d83aa71b4f8a99c13334df0f29d5
Source dataset
uspto-grants-1993_02
Patent number
US05187156

Reaction notes

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