Ammonia → HCID 22808903, compound

HRID 1733657Notes

Reaction equation

HRID 1733657 reaction equation
[CH2:1]([O:8][C:9](N[C@H](C(O)=O)CC1C=CC=CC=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:25]([CH2:28][CH3:29])CC)C.CS(ON1[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=2N=N1)(=O)=O.[NH3:44].[O:45]1CCC[CH2:46]1>>[CH2:1]([O:8][C:9]([NH:44][C:46](=[O:45])[C@H:28]([CH2:29][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[NH2:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 11745953Methanesulfonic acid, 1H-benzotriazol-1-yl ester

Product 1

HCID 22808903HCID 22808903, compound

Procedure

N-Benzyloxycarbonyl-L-phenylalanine (1.5 g) and triethylamine (0.7 ml) are dissolved in anhydrous tetrahydrofuran (20 ml). To the solution is added 1-methanesulfonyloxy-1,2,3-benzotriazole (1.10 g) at room temperature and the mixture is stirred for 1 hour, and thereto is further added 28% aqueous ammonia (3.0 ml) and the mixture is stirred for 2 hours. After allowing to stand, the solvent is distilled off under a reduced pressure, and to the residue is added water and the crystals are crushed. The crystals are separated by filtration, washed with water and dried to give N-benzyloxycarbonyl-L-phenylalaninamide (1.15 g), melting point: 158°-160° C. The product is identified with an authentic sample by infrared spectrum.

Workup

  1. stirringthe mixture is stirred for 2 hours
  2. distillationthe solvent is distilled off under a reduced pressure
  3. additionto the residue is added water
  4. customthe crystals are crushed
  5. customThe crystals are separated by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-202863d143fe42b89ab45e5a76acbcc4
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

Loading…