Trifluoroacetic acid → HCID 68309930, compound

HRID 922415Notes

Reaction equation

HRID 922415 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:16]([N:18]([CH:34]2[CH2:36][CH2:35]2)[C:19]([C@@H:21]2[O:26][CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22]2)=[O:20])[CH3:17])[CH:5]=[C:6]([O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[C:7]=1[O:8][CH3:9].FC(F)(F)C(O)=O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C@H:16]([N:18]([CH:34]2[CH2:36][CH2:35]2)[C:19]([C@@H:21]2[O:26][CH2:25][CH2:24][NH:23][CH2:22]2)=[O:20])[CH3:17])[CH:5]=[C:6]([O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[C:7]=1[O:8][CH3:9].[Br:1][C:2]1[CH:3]=[C:4]([C@@H:16]([N:18]([CH:34]2[CH2:36][CH2:35]2)[C:19]([C@@H:21]2[O:26][CH2:25][CH2:24][NH:23][CH2:22]2)=[O:20])[CH3:17])[CH:5]=[C:6]([O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[C:7]=1[O:8][CH3:9]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68309929HCID 68309929, compound

Product 2

HCID 68309930HCID 68309930, compoundHCID 68309931HCID 68309931, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (2R)-2-{[{1-[3-bromo-4-methoxy-5-(3-methoxypropoxy)-phenyl]ethyl}(cyclopropyl)amino]carbonyl}morpholine-4-carboxylate (135 mg) in dichloromethane (2 mL) was added trifluoroacetic acid (2 mL), and the mixture was stirred at room temperature for 30 minutes. The reaction solution was concentrated under reduced pressure, and to the resulting residue was added chloroform, and the mixture was filtered through (Bond-Elute: registered trademark) (NH2). The filtrate was concentrated under reduced pressure, and the resulting residue was purified by NH-silica gel column chromatography (eluent: ethyl acetate/methanol/ammonia water=200/10/1) to give (2R)-N-{(1R)-1-[3-bromo-4-methoxy-5-(3-methoxypropoxy)phenyl]ethyl}-N-cyclopropylmorpholine-2-carboxamide [Ex(5-1)] (53.7 mg) and (2R)-N-{(1S)-1-[3-bromo-4-methoxy-5-(3-methoxypropoxy)phenyl]ethyl}-N-cyclopropylmorpholine-2-carboxamide [Ex(5-2)] (30.5 mg) as a colorless oil.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionto the resulting residue was added chloroform
  3. filtrationthe mixture was filtered through (Bond-Elute: registered trademark) (NH2)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe resulting residue was purified by NH-silica gel column chromatography (eluent: ethyl acetate/methanol/ammonia water=200/10/1)

Sources & evidence

ORD record
ord-e3552eac42d2437dbc13a0b9275be95c
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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