Trifluoroacetic acid → HCID 69150976, compound

HRID 489678Notes

Reaction equation

HRID 489678 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:27][C:28]([C@@H:30]2[CH2:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:32][N:31]2C(OC(C)(C)C)=O)=[O:29])[C:10]([N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH2:24][CH2:25][OH:26])[CH2:14][CH2:13]2)=[O:11])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C@@H:9]([NH:27][C:28]([C@@H:30]2[CH2:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:32][NH:31]2)=[O:29])[C:10]([N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH2:24][CH2:25][OH:26])[CH2:14][CH2:13]2)=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69153176HCID 69153176, compound

Product 1

HCID 69150976HCID 69150976, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure described in Example 3 (Step b) using tert-butyl 3-[N-((1R)-1-[(4-chlorophenyl)methyl]-2-(4-[2-(hydroxyethyl)phenyl]-piperidyl]-2-oxoethyl)carbamoyl]-(3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (Step f) (323 mg, 0.5 mmol) and 50% TFA in CH2Cl2 (20 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 100% CH3CN (0.1% TFA) for 2 min] provided the title compound (TFA salt) as a white solid (145 mg). MS (ESI, pos. ion) m/z: 546 (M+1); (ESI, neg. ion) m/z: 544 (M−1). Calc'd for C32H36ClN3O3: 545.24.

Workup

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

Sources & evidence

ORD record
ord-cbdb255792664524b57aa82374180b05
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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