Trifluoroacetic acid → 3(S)-(2-((2(S)-Benzoylamino-3-methylbutyryl)benzylamino)acetylamino)-4-(4-(2,6-dichlorophenyl)-oxazol-2-yl)-4-oxobutyric Acid

HRID 1456653Notes

Reaction equation

HRID 1456653 reaction equation
C([O:5][C:6](=[O:51])[CH2:7][C@H:8]([NH:24][C:25](=[O:50])[CH2:26][N:27]([C:35](=[O:49])[C@@H:36]([NH:40][C:41](=[O:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH:37]([CH3:39])[CH3:38])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:9]([C:11]1[O:12][CH:13]=[C:14]([C:16]2[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:23])[N:15]=1)=[O:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:41]([NH:40][C@@H:36]([CH:37]([CH3:39])[CH3:38])[C:35]([N:27]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:26][C:25]([NH:24][C@H:8]([C:9]([C:11]1[O:12][CH:13]=[C:14]([C:16]2[C:17]([Cl:23])=[CH:18][CH:19]=[CH:20][C:21]=2[Cl:22])[N:15]=1)=[O:10])[CH2:7][C:6]([OH:51])=[O:5])=[O:50])=[O:49])(=[O:48])[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 541815803(S)-(2-((2(S)-Benzoylamino-3-methylbutyryl)benzylamino)acetylamino)-4-(4-(2,6-dichlorophenyl)-oxazol-2-yl)-4-oxobutyric Acid tert-Butyl Ester

Product 1

HCID 536861393(S)-(2-((2(S)-Benzoylamino-3-methylbutyryl)benzylamino)acetylamino)-4-(4-(2,6-dichlorophenyl)-oxazol-2-yl)-4-oxobutyric Acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 709 in CH2Cl2 (4.0 mL) was added TFA (2.0 mL) and the reaction stirred at rt for 1 hr. The reaction was concentrated in vacuo and the residue co-concentrated with toluene. Prep-HPLC provided 35 mg of compound 710: 1H NMR (500 MHz, CD3 OD) δ 8.90 (m), 8.52 (m), 8.35 (m), 7.83 (m), 7.62-7.39 (m), 7.38-7.16 (m), 5.52 (m), 5.01 (m), 5.01 (m), 4.99-4.53 (m), 4.42 (m), 4.33-3.82 (m), 3.16-2.93 (m), 2.91-2.48 (m), 2.24 (m), 1.09-0.85 (m). ##STR89##

Workup

  1. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-cb7a0f34b03a46ddbddd31ef601f8435
Source dataset
uspto-grants-1998_12
Patent number
US05843904

Reaction notes

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