Trifluoroacetic acid → N-[(Benzyloxy)carbonyl]-L-phenylalanyl-L-leucinamide

HRID 1378906Notes

Reaction equation

HRID 1378906 reaction equation
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:23][C@H:24]([C:29]([NH2:31])=[O:30])[CH2:25][CH:26]([CH3:28])[CH3:27].FC(F)(F)C(O)=O>>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([NH:23][C@H:24]([C:29]([NH2:31])=[O:30])[CH2:25][CH:26]([CH3:28])[CH3:27])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 69640LeucinamideHCID 70878Benzyloxycarbonyl-L-phenylalanine

Product 1

HCID 13386706N-[(Benzyloxy)carbonyl]-L-phenylalanyl-L-leucinamide

Procedure

30 mg (0.1 mole) Z-Phe-OH and 13 mg (0.1 mmole) Leu-NH2 are placed into an unsealed glass container having a 12 mm inner diameter and stirred with a spatula. Then, a mixture of 161 mg (0.5 mole) Na2 SO4.10H2O and 5 mg thermolysine is added, the glass container is closed and subjected to ultrasonic waves in an ultrasound bath at 40° C. After 20 minutes the reaction is stopped with 0.4 ml 5% (v/v) aqueous trifluoroacetic acid. The analytical evaluation is carried out by means of HPLC and comparison with an authentic specimen.

Workup

  1. additionis added
  2. customthe glass container is closed
  3. customsubjected to ultrasonic waves in an ultrasound bath at 40° C

Sources & evidence

ORD record
ord-4c87cbe974114306830a660ab60e3eb4
Source dataset
uspto-grants-1997_09
Patent number
US05670332

Reaction notes

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