Trifluoroacetic acid → HCID 10270779, compound

HRID 1698900Notes

Reaction equation

HRID 1698900 reaction equation
C([NH:8][CH2:9][C:10]([NH:12][CH2:13][C:14]1[S:15][C:16]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:17][C:18]=1[NH:19][C:20]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=1)=[O:21])=[O:11])(OC(C)(C)C)=O.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][CH2:9][C:10]([NH:12][CH2:13][C:14]1[S:15][C:16]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:17][C:18]=1[NH:19][C:20]([NH:22][C:23]1[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=1)=[O:21])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10277134HCID 10277134, compound

Product 1

HCID 10270779HCID 10270779, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2-(N-(N-carbo-tert-butoxyglycyl)aminomethyl)-5-tert-butyl-3-thienyl)-N′-(4-methylphenyl)urea (0.050 g, 0.105 mmol) in CH2Cl2 (3 mL) at room temp. was added trifluoroacetic acid (0.50 mL, 6.49 mmol, 62 equiv). The resulting mixture was stirred for 3 h, washed with a saturated NaHCO3 solution, dried (MgSO4), and concentrated under reduced pressure. The residue was purified by flash chromatography (for CH2Cl2 to 20% MeOH/CH2Cl2) to give N-(2-(N-glycylaminomethyl)-5-tert-butyl-3-thienyl)-N′-(4-methylphenyl)urea (0.019 g, 48%): mp 93-6° C.; 1H NMR (CDCl3) δ1.14 (s, 9H), 2.08 (s, 3H), 3.89 (s, 2H), 4.34 (br s, 7H), 6.67 (s, 1H), 6.87 (d, J=8.1 Hz, 2H), 7.12 (d, J=8.5 Hz, 2H), 7.3 (m, 2H).

Workup

  1. washwashed with a saturated NaHCO3 solution
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography (for CH2Cl2 to 20% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-eef87a78629f42ddb3b88c351382374c
Source dataset
uspto-grants-2002_02
Patent number
US06344476B1

Reaction notes

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