Trifluoroacetic acid → 3(S)-(2-((2(S)-Benzoylamino-3-methylbutyryl)benzylamino)acetylamino)-4-oxo-butyric Acid

HRID 1456650Notes

Reaction equation

HRID 1456650 reaction equation
C([O:5][C:6](=NNC(N)=O)[CH2:7][C@H:8]([NH:11][C:12](=[O:37])[CH2:13][N:14]([C:22](=[O:36])[C@@H:23]([NH:27][C:28](=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH:24]([CH3:26])[CH3:25])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:9]=[O:10])(C)(C)C.C(O)(C(F)(F)F)=[O:44]>C(Cl)Cl>[C:28]([NH:27][C@@H:23]([CH:24]([CH3:26])[CH3:25])[C:22]([N:14]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:13][C:12]([NH:11][C@H:8]([CH:9]=[O:10])[CH2:7][C:6]([OH:5])=[O:44])=[O:37])=[O:36])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 545745803(S)-(2-((2(S)-Benzoylamino-3-methylbutyryl)benzylamino)acetylamino)-4-oxo-butyric Acid tert-Butyl Ester Semicarbazone

Product 1

HCID 544052433(S)-(2-((2(S)-Benzoylamino-3-methylbutyryl)benzylamino)acetylamino)-4-oxo-butyric Acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of compound 705 (600 mg, 1.04 mmol) in CH2Cl2 (10 mL) was added TFA (4.0 mL) and the reaction allowed to stir for 4 hr. The reaction was concentrated in vacuo and the residue co-concentrated with toluene (3×). The residue was dissolved in MeOH (10 mL) and treated with HOAc (2.0 mL) followed by formaldehyde (2.0 mL). After stirring for 3 hr at rt, the reaction was concentrated in vacuo. Prep-HPLC provided 89 mg of compound 706: 1H NMR (500 MHz, CD3OD) 68.34-8.21 (m), 7.80-7.69 (m), 7.51-7.02 (m), 4.99-4.81 (m), 4.73-4.59 (m), 4.57-4.56 (m), 4.35-4.12 (m), 4.07-3.96 (m), 3.93-3.84 (m), 2.64-2.51 (m), 2.49-2.31 (m), 2.29-2.13 (m), 1.02-0.80 (m). ##STR85##

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionThe residue was dissolved in MeOH (10 mL)
  3. additiontreated with HOAc (2.0 mL)
  4. stirringAfter stirring for 3 hr at rt
  5. concentrationthe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-837a6b216c36401d911878a602bb0ed0
Source dataset
uspto-grants-1998_12
Patent number
US05843904

Reaction notes

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