Trifluoroacetic acid → HCID 178463220, compound

HRID 2053722Notes

Reaction equation

HRID 2053722 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C@@H:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([N:24]=[C:25]([NH:27][CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[C:32]([F:37])[CH:31]=3)[CH3:26])[CH:22]=2)[CH2:17][C@H:16]1[OH:38])(C)(C)C.O=C1CCC(=O)N1O[C:48]([C:50]1[CH:55]=[CH:54][C:53]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)=[CH:52][C:51]=1[F:62])=[O:49].C(N(CC)CC)C>C(Cl)Cl>[F:37][C:32]1[CH:31]=[C:30]([CH:35]=[CH:34][C:33]=1[F:36])[CH2:29][CH2:28][NH:27][C:25](=[N:24][C:21]1[CH:22]=[C:23]2[C:18]([CH2:17][C@@H:16]([OH:38])[C@@H:15]2[NH:14][C:48]([C:50]2[CH:55]=[CH:54][C:53]([C:56]3[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=3)=[CH:52][C:51]=2[F:62])=[O:49])=[CH:19][CH:20]=1)[CH3:26]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 86595229HCID 86595229, compoundHCID 178463222HCID 178463222, compound

Product 1

HCID 178463220HCID 178463220, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add 5 mL of trifluoroacetic acid to (R)-(6-(1-((3,4-difluorobenzyl)methylamino)ethylideneamino)-2(R)-hydroxyindan-1-yl)carbamic acid tert-butyl ester (180 mg, 4.04 mmol) and stir for 30 minutes. Remove solvent under reduced pressure. Dissolve the residue in 15 mL of CH2Cl2. Then add 3-fluorobiphenyl-4-carboxylic acid 2,5-dioxopyrrolidin-1-yl ester (150 mg, 4.79 mmol) and triethylamine (0.6 mL, 4.0 mmol) to the solution and stir for 12 hours. Pour the mixture into methylene chloride, wash with water, dry with Na2SO4, and then concentrate. Purify the residue by column chromatography (silica gel, 3% MeOH in CH2Cl2) to give 35 mg of the title compound as a white solid in 16% yield: 1H NMR (CD3OD) δ 7.88 (2H, t, J=8.0 Hz), 7.7 (2H, d, J=8.4 Hz), 7.60 (2H, dd, J=8.0, 1.2 Hz), 7.47-7.55 (3H, m), 7.43-7.47 (1H, m), 7.21-7.32 (2H, m), 7.18 (1H, d, J=8.0 Hz), 7.11-7.14 (1H, m), 6.71 (2H, dd, J=10.0, 1.2 Hz), 5.47 (1H, d, J=6.8 Hz), 4.69 (2H, s), 4.54 (1H, q, J=7.2 Hz), 4.54 (1H, q, J=6.4 Hz), 3.29 (1H, q, J=7.2 Hz), 3.07 (3H, s), 2.88 (1H, q, J=7.8 Hz), 1.99 (3H, s); MS 544 (MH+).

Workup

  1. washwash with water
  2. dry with materialdry with Na2SO4
  3. concentrationconcentrate
  4. customPurify the residue by column chromatography (silica gel, 3% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-4e103d94891f4e73ac8aa0551858f9ea
Source dataset
uspto-grants-2008_02
Patent number
US07326731B2

Reaction notes

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