Water → HCID 53852973, compound

HRID 1733667Notes

Reaction equation

HRID 1733667 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([OH:22])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(O[N:35]1[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=2[N:37]=[N:36]1)(=O)=O.O>C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([O:22][N:35]1[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=2[N:37]=[N:36]1)=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 11745953Methanesulfonic acid, 1H-benzotriazol-1-yl ester

Product 1

HCID 53852973HCID 53852973, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

N-Benzyloxycarbonyl-L-phenylalanine (1.5 g) and triethylamine (0.7 ml) are dissolved in ethyl acetate (15 ml). To the solution is added 1-methanesulfonyloxy-1,2,3-benzotriazole (1.1 g) under ice-cooling and the mixture is stirred for 1 hour. After allowing to stand overnight, to the reaction mixture are added ethyl acetate and water. The ethyl acetate layer is separated, washed with water and dried over anhydrous magnesium sulfate. After drying, the solvent is distilled off and to the residue is added ether. The precipitated crystals are separated by filtration to give 1-(N-benzyloxycarbonyl-L-phenylalanyloxy)-1,2,3-benzotriazole (1.3 g), melting point: 120°-125° C.

Workup

  1. temperaturecooling
  2. waitto stand overnight, to the reaction mixture
  3. customThe ethyl acetate layer is separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter drying
  7. distillationthe solvent is distilled off and to the residue
  8. additionis added ether
  9. customThe precipitated crystals are separated by filtration

Sources & evidence

ORD record
ord-4b7fb15ed4bf410cb3beb510485ab01e
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

Loading…