Acetic Acid → HCID 18511143, compound

HRID 635681Notes

Reaction equation

HRID 635681 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[C:18](OC(NC(=NC(OC(C)(C)C)=O)SC)=O)(C)(C)C.C(O)(=O)C>CO>[NH2:1][C:2]1[C:6]([CH3:18])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5466031,3-DI-Boc-2-methylisothioureaHCID 10751930Ethyl 3-amino-5-phenyl-1H-pyrrole-2-carboxylate

Product 1

HCID 18511143HCID 18511143, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 25-mL, round-bottomed flask was added ethyl 3-amino-5-phenylpyrrole-2-carboxylate (Example 66(b)) (1.1 g) and MeOH (5 mL). To the reaction flask was added 1,3-bis(tertbutoxycarbonyl)-2-methyl-2-thiopseudourea (Aldrich Chemical Company) (1.6 g, 5.5 mmol), followed by glacial acetic acid (1.43 mL, 25 mmol). The reaction mixture was stirred at room temperature under N2 for 28 h. A heavy precipitate formed and was collected by filtration, washed with H2O (3×10 mL) and dried in a vacuum oven overnight to give 0.71 g (32% from Example 66(a)) of the title compound as an off-white solid. 1H NMR (DMSO-d6; 400 MHz): δ 1.38 (t, 3, J=7.00), 1.44 (s, 9), 1.46 (s, 9), 4.38 (q, 2, J=6.97), 7.31-7.46 (m, 3), 7.76 (d, 2, J=7.86), 11.06 (br s, 1), 11.25 (s, 1), 11.61 (s, 1), 11.95 (br s, 1); MS m/z: 473 (M+1), 471 (M−1).

Workup

  1. customA heavy precipitate formed
  2. filtrationwas collected by filtration
  3. washwashed with H2O (3×10 mL)
  4. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-60288b91379f4121a6cf876ed3913f86
Source dataset
uspto-grants-2001_02
Patent number
US06187777B1

Reaction notes

Loading…