Trifluoroacetic acid methylene chloride → HCID 67382333, compound

HRID 913052Notes

Reaction equation

HRID 913052 reaction equation
[CH2:1]([C:3]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([C:16]2[NH:17][C:18]([C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=3)=[CH:19][N:20]=2)[CH2:14][OH:15])OCC[O:4]1)[CH3:2].C(Cl)Cl.[C:34]([OH:40])([C:36]([F:39])([F:38])[F:37])=[O:35]>>[F:37][C:36]([F:39])([F:38])[C:34]([O-:40])=[O:35].[OH:15][CH2:14][CH:13]([C:16]1[NH:17][C:18]([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)=[CH:19][NH+:20]=1)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:3](=[O:4])[CH2:1][CH3:2]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 67382133HCID 67382133, compound

Product 1

HCID 67382333HCID 67382333, compound

Procedure

The alcohol C1 was dissolved in DCM/TFA (8:2, 0.03 M solution) and the solution was stirred for 2 hr and then the solvents were removed under reduced pressure and the crude was purified by preparative RP-HPLC (column: C18), using H2O (0.1% TFA) and MeCN (+0.1% TFA) as eluents. The desired fractions were lyophilized to yield a white powder. 1H NMR (400 MHz, DMSO-d6) δ: 14.41 (1H, bs), 8.40 (1H, s), 8.22 (1H, s), 8.15-8.06 (1H, m), 8.03-7.92 (3H, m), 7.70-7.54 (2H, m), 3.70 (2H, d, J=5.9 Hz), 3.32-3.19 (1H, m), 2.47-2.32 (4H, m), 1.88-1.72 (2H, m), 1.56-1.40 (2H, m), 1.35-1.15 (4H, m), 0.92 (3H, t, J=7.2 Hz). MS (ES) C23H28N2O2 requires: 364, found: 365 (M+H)+.

Workup

  1. customthe solvents were removed under reduced pressure
  2. customthe crude was purified by preparative RP-HPLC (column: C18)
  3. customto yield a white powder

Sources & evidence

ORD record
ord-52f22eae2ddb4b9389037b307be26fd0
Source dataset
uspto-grants-2011_09
Patent number
US08026265B2

Reaction notes

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