Trifluoroacetic acid → HCID 10117666, compound

HRID 489680Notes

Reaction equation

HRID 489680 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:44])[C@H:16]([NH:24][C:25]([C@@H:27]2[CH2:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:29][N:28]2C(OC(C)(C)C)=O)=[O:26])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:11][CH2:10]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:29]1[C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:36][C@@H:27]([C:25]([NH:24][C@H:16]([CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:15]([N:12]2[CH2:13][CH2:14][CH:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[CH2:10][CH2:11]2)=[O:44])=[O:26])[NH:28]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69741513HCID 69741513, compound

Product 1

HCID 10117666HCID 10117666, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure described in Example 3 (Step b) from tert-butyl (3S)-3-(N-((1R)-2-[4-(2-methoxyphenyl)piperidyl]-2-oxo-1-benzylethyl]carbamoyl)-1,2,3,4-tetrahydro-isoquinoline-2-carboxylate (Step b) (1.4 g, 2.34 mmol) and 50% TFA in CH2Cl2 (80 mL). Purification by reverse phase preparative HPLC [Phenomenex; 5 μm 250×21.2 mm, 5% to 95% CH3CN (0.1% TFA) in H2O (0.1% TFA) over 30 min, then 10U % CH3CN (0.1% TFA) for 2 min] provided the title compound (TFA salt) as a white foam (0.5 g). MS (ESI, pos. ion) m/z: 498 (M+1). Calc'd for C31H35N3O3: 497.27.

Workup

  1. customThe title compound was prepared
  2. customPurification by reverse phase preparative HPLC [Phenomenex

Sources & evidence

ORD record
ord-cb685c0ec7704f80b38d9d4f7423119e
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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