Trifluoroacetic acid → Methyl p-aminophenylcarbamate

HRID 1467796Notes

Reaction equation

HRID 1467796 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:19])[O:10][CH2:11]C(OC(C)(C)C)=O)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:19])[O:10][CH3:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89499961HCID 89499961, compound

Product 1

HCID 80938Methyl p-aminophenylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Intermediate 10A (2.6 g, 9.77 mmol) was deprotected with 30% TFA in DCM (40 mL). After 2H, the reaction was concentrated and the residue was partitioned with EtOAc (75 mL) and saturated NaHCO3 (50 mL). The organic layer was washed with brine (20 mL) and dried (MgSO4). Crude Intermediate 10B was carried onto the next step. 1H NMR (400 MHz, DMSO-d6) δ 9.86 (1H, s), 7.56 (2H, d, J=8.84 Hz), 7.28 (2H, d, J=8.84 Hz), 6.90 (2H, s), 3.68 (3H, s) ppm.

Workup

  1. concentrationAfter 2H, the reaction was concentrated
  2. customthe residue was partitioned with EtOAc (75 mL) and saturated NaHCO3 (50 mL)
  3. washThe organic layer was washed with brine (20 mL)
  4. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-d46c17c356f04099aa57f51af82cdf9c
Source dataset
uspto-grants-2015_04
Patent number
US09000172B2

Reaction notes

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