Trifluoroacetic acid → HCID 178463262, compound

HRID 1668501Notes

Reaction equation

HRID 1668501 reaction equation
[CH2:1]([N:3]([CH:11]1[CH2:16][CH2:15][C:14]([C:17]2[C:25]3[C:20](=[CH:21][C:22]([NH:26][C:27]([C:29]4[S:30][CH:31]=[CH:32][CH:33]=4)=[NH:28])=[CH:23][CH:24]=3)[NH:19][CH:18]=2)=[CH:13][CH2:12]1)C(=O)OC(C)(C)C)[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([NH:3][CH:11]1[CH2:16][CH2:15][C:14]([C:17]2[C:25]3[C:20](=[CH:21][C:22]([NH:26][C:27]([C:29]4[S:30][CH:31]=[CH:32][CH:33]=4)=[NH:28])=[CH:23][CH:24]=3)[NH:19][CH:18]=2)=[CH:13][CH2:12]1)[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178465426HCID 178465426, compound

Product 1

HCID 178463262HCID 178463262, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of compound 131 (0.08 g, 0.172 mmol) was treated with 20% TFA in CH2Cl2 (10 mL) at 0° C. and stirring was continued for 2 h at same temperature. Solvent was evaporated and crude was diluted with 10% aq. NH4OH (25 mL) and product was extracted into CH2Cl2 (2 20 mL). The combined CH2Cl2 layer washed with brine (15 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2M NH3 in MeOH: CH2Cl2, 1:9) to obtain compound 132 (0.055 g, 89%) as a solid. Compound was repurified using reverse phase column chromatography (CH3CN: pH 10.6 buffer, 20:80 to 55:45) on biotage to obtain pure product. mp 95-97° C.; 1H NMR (DMSO-d6) δ 1.04 (t, 3H, J=7.2 Hz), 1.38-1.49 (m, 1H), 1.91-1.99 (m, 2H), 2.40-2.48 (m, 2H), 2.56-2.80 (m, 4H), 6.07 (s, 1H), 6.30 (s, 2H), 6.59 (d, 1H, J=8.4 Hz), 6.81 (s, 1H), 7.09 (t, 1H, J=4.5 Hz), 7.20 (d, 1H, J=2.1 Hz), 7.59 (d, 1H, J=5.1 Hz), 7.68-7.72 (m, 2H), 10.80 (s, 1H); ESI-MS (m/z, %) 365 (MH+, 7), 160 (50), 119 (100); ESI-HRMS calculated for C21H25N4S (MH+), calculated: 365.1794; observed: 365.1801.

Workup

  1. customSolvent was evaporated
  2. additioncrude was diluted with 10% aq. NH4OH (25 mL) and product
  3. extractionwas extracted into CH2Cl2 (2 20 mL)
  4. washThe combined CH2Cl2 layer washed with brine (15 mL)
  5. dry with materialdried (Na2SO4)
  6. customSolvent was evaporated
  7. customcrude was purified by column chromatography (2M NH3 in MeOH: CH2Cl2, 1:9)

Sources & evidence

ORD record
ord-a112afbde9274a518fbf23cb4c85adbe
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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