Trifluoroacetic acid → (R)-2-((S)-2-(4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzamido)-3-methylbutanamido)propanoic acid

HRID 594194Notes

Reaction equation

HRID 594194 reaction equation
[O:1]=[C:2]1[CH:6]=[CH:5][C:4](=[O:7])[N:3]1[C:8]1[CH:32]=[CH:31][C:11]([C:12]([NH:14][C@@H:15]([CH:28]([CH3:30])[CH3:29])[C:16]([NH:18][C@@H:19]([CH3:27])[C:20]([O:22]C(C)(C)C)=[O:21])=[O:17])=[O:13])=[CH:10][CH:9]=1.FC(F)(F)C(O)=O.C(OCC)(=O)C>ClCCl.CCCCCC>[O:7]=[C:4]1[CH:5]=[CH:6][C:2](=[O:1])[N:3]1[C:8]1[CH:32]=[CH:31][C:11]([C:12]([NH:14][C@@H:15]([CH:28]([CH3:29])[CH3:30])[C:16]([NH:18][C@H:19]([CH3:27])[C:20]([OH:22])=[O:21])=[O:17])=[O:13])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 67451966(S)-tert-butyl 2-((S)-2-(4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzamido)-3-methylbutanamido)propanoate

Product 1

HCID 67450926(R)-2-((S)-2-(4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzamido)-3-methylbutanamido)propanoic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a mixture of 100 (47 mg, 0.11 mmol) in dichloromethane (5 mL) was added trifluoroacetic acid (5 mL) and the reaction mixture was monitored by TLC (50% ethyl acetate in hexane, after pumping down the TLC plate under high vacuum for 5 min). After 75 min, no starting material could be detected by TLC. The reaction was performed a second time using the same conditions and material from both reactions were combined and purified on a 2 mm radial chromatotron plate eluting with a gradient from 5-10% methanol in dichloromethane. The yield was 42 mg (49%) of 53: 1H-NMR (400 MHz, CDCl3) δ 7.92 (d, J=6.6 Hz, 2H), 7.51 (d, J=6.6 Hz, 2H), 7.0 (m, 1H), 6.89 (s, 2H), 6.70 (s, 1H), 4.60 M, 1H), 2.22 (m, 1H), 1.18 (d, J=6.6 Hz, 3H), 1.04 (m, 6H); MS (ES+) m/z 388.02 [M+H]+.

Workup

  1. customfor 5 min
  2. custompurified on a 2 mm radial chromatotron plate
  3. washeluting with a gradient from 5-10% methanol in dichloromethane

Sources & evidence

ORD record
ord-34840a9ebb4e4fc08464f5d37588b103
Source dataset
uspto-grants-2016_01
Patent number
US09242013B2

Reaction notes

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