Trifluoroacetic acid → Methyl p-aminophenylcarbamate

HRID 515763Notes

Reaction equation

HRID 515763 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 2 h, 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 (1 H, s), 7.56 (2 H, d, J=8.84 Hz), 7.28 (2 H, d, J=8.84 Hz), 6.90 (2 H, s), 3.68 (3 H, s) ppm.

Workup

  1. concentrationthe 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-89a32b3905704f7c9d1bdc85abd3a63d
Source dataset
uspto-grants-2015_08
Patent number
US09108951B2

Reaction notes

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