Sodium Hydroxide → HCID 67253744, compound

HRID 2207464Notes

Reaction equation

HRID 2207464 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[C:19]([C:23]([O:25]C)=[O:24])[N:20]([CH3:22])[CH:21]=2)=[CH:13][CH:12]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>O1CCOCC1>[C:3]([O:7][C:8]([NH:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:18]=[C:19]([C:23]([OH:25])=[O:24])[N:20]([CH3:22])[CH:21]=2)=[CH:15][CH:16]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67253196Methyl 4-(4-(tert-butoxycarbonylamino)phenyl)-1-methyl-1H-pyrrole-2-carboxylate

Product 1

HCID 67253744HCID 67253744, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 0.5 M solution of NaOH (2.0 eq) was added to a solution of 5 (1.0 g, 3.027 mmol) in dioxane (40 mL). The reaction mixture was allowed to stir at room temperature for 6 hours at which point TLC revealed completion of reaction. Excess 1,4-dioxane was evaporated under vacuum and the residue was diluted with water. The resulting solution was acidified with 0.5 M HCl. The product was extracted from water with 2× ethyl acetate (100 mL×2) and the organic layers were combined, washed with brine, dried over MgSO4 and concentrated in vacuo. The product was purified using flash chromatography (ethyl acetate/n-hexane 2:8). Yield—0.92 g, 96.8%. IR (FTIR, vmax/cm−1): 3371, 2979, 1698, 1671, 1522, 1445, 1367, 1285, 1161, 1112, 1047, 823, 803, 762, 714, 631; 1H-NMR (400 MHz, CDCl3): δ 8.33 (1H, s), 7.55 (d, 2H, J=8.8 Hz), 7.50 (d, 2H, J=8.8 Hz), 7.36 (d, 1H, J=2.0 Hz), 7.22 (d, 1H, J=2.0), 3.97 (s, 3H), 1.50 (s, 9H); 13C-NMR (100 MHz, CDCl3): δ 162.3, 153.7, 138.6, 123.0, 127.1, 126.0, 124.4, 124.0, 119.5, 115.1, 79.9, 36.9, 28.6; EIMS m/z (+EI) calc. for C17H20N2O4 (M)+ 316.35. found 315.16 (M+H)+.

Workup

  1. customcompletion of reaction
  2. customExcess 1,4-dioxane was evaporated under vacuum
  3. additionthe residue was diluted with water
  4. extractionThe product was extracted from water with 2× ethyl acetate (100 mL×2)
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe product was purified

Sources & evidence

ORD record
ord-6402c4f5cda049b8a1dcdc89cf559097
Source dataset
uspto-grants-2016_06
Patent number
US09376440B2

Reaction notes

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