Hydrochloric Acid → HCID 9809334, compound

HRID 2082224Notes

Reaction equation

HRID 2082224 reaction equation
Cl.[NH2:2][C@H:3]([C:7]([NH:9][C@@H:10]([C:23]([NH:25][C@H:26]([C:34]([N:36]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH3:37])=[O:35])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:24])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH:21]=[O:22])[CH:13]=1)=[O:8])[C@@H:4]([CH3:6])[OH:5].C(N(CC)CC)C.[CH3:52][C:53](OC(C)=O)=[O:54]>C(Cl)Cl>[NH:2]([C:53]([CH3:52])=[O:54])[C@H:3]([C:7]([NH:9][C@@H:10]([C:23]([NH:25][C@H:26]([C:34]([N:36]([CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[CH3:37])=[O:35])[CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:24])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH:21]=[O:22])[CH:13]=1)=[O:8])[C@@H:4]([CH3:6])[OH:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 101632290HCID 101632290, compound

Product 1

HCID 9809334HCID 9809334, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of HCl.H-Thr-D-Trp(CHO)-Phe-NMeBzl (2.29 g) in methylene chloride (30 ml), were added triethylamine (747 mg) and Ac2O (377 mg) at -20° C. The reaction mixture was stirred for 45 minutes at the same temperature, and washed successively with water, diluted sodium hydrogencarbonate solution, water, 0.5N hydrochloric acid, and sodium chloride solution and dried over magnesium sulfate. After concentration, the residue was dissolved in 65% aqueous ethanol (45 ml) under heating, and the solution was left standing overnight at room temperature. The resulting needles were filtered, washed with 65% aqueous ethanol, and dried to give Ac-Thr-D-Trp(CHO)-Phe-NMeBzl (1.92 g).

Workup

  1. washwashed successively with water, diluted sodium hydrogencarbonate solution, water, 0.5N hydrochloric acid, and sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. concentrationAfter concentration
  4. dissolutionthe residue was dissolved in 65% aqueous ethanol (45 ml)
  5. temperatureunder heating
  6. waitthe solution was left
  7. waitstanding overnight at room temperature
  8. filtrationThe resulting needles were filtered
  9. washwashed with 65% aqueous ethanol
  10. customdried

Sources & evidence

ORD record
ord-e39596f17912496395b17b19d1d43275
Source dataset
uspto-grants-1993_02
Patent number
US05187156

Reaction notes

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