Trifluoroacetic acid → HCID 86618170, compound

HRID 2242668Notes

Reaction equation

HRID 2242668 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:22]([N:24]1[CH2:28][CH2:27][C@H:26]([F:29])[CH2:25]1)=[O:23])[C@H:9]([CH:11]1[CH2:16][CH2:15][CH:14]([N:17]([C:19](=[O:21])[CH3:20])[CH3:18])[CH2:13][CH2:12]1)[CH3:10])(C)(C)C.[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34]>ClCCl>[F:31][C:32]([F:37])([F:36])[C:33]([O-:35])=[O:34].[C:19]([N:17]([CH3:18])[CH:14]1[CH2:13][CH2:12][CH:11]([C@H:9]([CH3:10])[C@H:8]([NH3+:7])[C:22]([N:24]2[CH2:28][CH2:27][C@H:26]([F:29])[CH2:25]2)=[O:23])[CH2:16][CH2:15]1)(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131727929HCID 131727929, compound

Product 1

HCID 86618170HCID 86618170, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the material prepared in Step D (0.012 g, 0.028 mmol) in dichloromethane (3 mL) was added trifluoroacetic acid (1 mL). After 3 h at ambient temperature the reaction was concentrated in vacuo, affording the title compound as a white solid. 1H NMR (500 MHz, CD3OD): δ 5.41 (s, 0.5H as a single rotamer), 5.36 (s, 0.5H as a single rotamer), 5.31 (0.5H as a single rotamer), 5.26 (0.5H as a single rotamer), 4.28 (m, 1H), 4.06 (dd, J=5.5 Hz, J=9.0 Hz, 1H), 4.00 (dd, J=5.5 Hz, J=9.0 Hz, 1H), 3.78 (m, 6H), 3.64 (m, 2H), 3.51 (m, 1H), 2.90 (s, 1.5H as a single rotamer), 2.79 (s, 1.5H as a single rotamer), 2.31 (m, 2H), 2.13 (s, 3H), 2.07 (s, 3H), 1.98 (m, 2H), 1.70 (m, 6H), 1.30 (m, 2H), 0.93 (m, 3H); LC/MS 328.3 (M+1).

Workup

  1. concentrationAfter 3 h at ambient temperature the reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-20f26a1813f04f74a7d98fc0916ca8bf
Source dataset
uspto-grants-2010_03
Patent number
US07671073B2

Reaction notes

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