Trifluoroacetic acid → HCID 67114038, compound

HRID 1507665Notes

Reaction equation

HRID 1507665 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1([OH:34])[CH2:8][CH2:7][CH2:6][CH:5]1[C:9]([NH:11][C@H:12]([CH:31]([CH3:33])[CH3:32])[C:13]([N:15]1[CH2:20][CH2:19][C@@:18]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)([OH:21])[C:17]([CH3:30])([CH3:29])[CH2:16]1)=[O:14])=[O:10].C(N(CC)CC)C.[C:42](N1C=CN=C1)(N1C=CN=C1)=[O:43].C(O)(C(F)(F)F)=O>C1COCC1.O.CO>[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([C@@:18]2([OH:21])[CH2:19][CH2:20][N:15]([C:13](=[O:14])[C@H:12]([NH:11][C:9]([CH:5]3[C:4]4([CH2:3][CH2:2][NH:1][C:42](=[O:43])[O:34]4)[CH2:8][CH2:7][CH2:6]3)=[O:10])[CH:31]([CH3:32])[CH3:33])[CH2:16][C:17]2([CH3:29])[CH3:30])=[CH:27][CH:26]=1

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acid2×HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 67113795HCID 67113795, compound

Product 1

HCID 67114038HCID 67114038, compoundYield 25%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-aminoethyl)-N-((R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-yl)-2-hydroxycyclopentanecarboxamide (from step G, 30 mg, 0.061 mmol) in THF (0.5 mL) was added triethylamine (0.017 mL, 0.121 mmol) and 1,1′-Carbonyldiimidazole (14.77 mg, 0.091 mmol) at room temperature. The resulting mixture was stirred at room temperature for 4 hours. The reaction mixture was subjected to preparative HPLC (Shimadzu VP-ODS 20×100 mm, 8 min. gradient, Solvent A: 10% MeOH, 90% H2O, 0.1% TFA; Solvent B: 90% MeOH, 10% H2O, 0.1% TFA). The fractions corresponding to each individual diasteromer were collected, concentrated and freeze dried to yield (isomer 1: 8 mg, 0.015 mmol, 25% yield; isomer 2: 6 mg, 0.011 mmol, 19% yield).

Workup

  1. customThe fractions corresponding to each individual diasteromer were collected
  2. concentrationconcentrated
  3. customfreeze dried
  4. customto yield (isomer 1: 8 mg, 0.015 mmol, 25% yield; isomer 2: 6 mg, 0.011 mmol, 19% yield)

Sources & evidence

ORD record
ord-85c19f13848b4b5283a5b2691b1e2940
Source dataset
uspto-grants-2015_12
Patent number
US09221819B2

Reaction notes

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