Trifluoroacetic acid → HCID 86606145, compound

HRID 254388Notes

Reaction equation

HRID 254388 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]([CH2:25][CH2:26][N:27]([CH2:33][C@H:34]([OH:37])[CH2:35][OH:36])[CH2:28][C@H:29]([OH:32])[CH2:30][OH:31])[CH2:20][C@H:21]([OH:24])[CH2:22][OH:23])=[CH:15][CH:14]=1)=O)(C)(C)C.[C:38]([OH:44])([C:40]([F:43])([F:42])[F:41])=[O:39]>ClCCl>[F:41][C:40]([F:43])([F:42])[C:38]([OH:44])=[O:39].[F:41][C:40]([F:43])([F:42])[C:38]([OH:44])=[O:39].[OH:32][C@H:29]([CH2:30][OH:31])[CH2:28][N:27]([CH2:26][CH2:25][N:19]([C:16]1[CH:17]=[CH:18][C:13]([CH2:12][CH2:11][CH2:10][CH2:9][NH2:8])=[CH:14][CH:15]=1)[CH2:20][C@H:21]([OH:24])[CH2:22][OH:23])[CH2:33][C@H:34]([OH:37])[CH2:35][OH:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58664820HCID 58664820, compound

Product 1

HCID 86606145HCID 86606145, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dichloromethane (2 mL) was added to the protected amine 670 (0.27 g, 0.5 mmol) followed by addition of TFA (5 mL). The mixture was stirred at room temperature for 25 min. The solvent was removed under reduced pressure. The residue was dissolved in methanol and the solvent was removed again under reduced pressure. The residue was dried under vacuum overnight to afford the compound 680 (0.31 g, 80%) as a clear oil. 1H NMR (300 MHz, CD3OD) δ 1.66 (m, 4H), 2.59 (m, 2H), 2.92 (m, 2H), 3.15-4.10 (m, 20H), 6.78 (d, 2H), 6.98 (d, 2H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in methanol
  3. customthe solvent was removed again under reduced pressure
  4. customThe residue was dried under vacuum overnight

Sources & evidence

ORD record
ord-05f0d4f9ad4b4be78d963372b581d912
Source dataset
uspto-grants-2011_01
Patent number
US07875619B2

Reaction notes

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