Trifluoroacetic acid → HCID 18470689, compound

HRID 2228562Notes

Reaction equation

HRID 2228562 reaction equation
C(OC([NH:8][C:9]1[C:10]([NH:22][C:23](=[O:34])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:11][C:12]([O:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:14]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:30]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:23]([NH:22][C:10]1[C:9]([NH2:8])=[CH:14][CH:13]=[C:12]([O:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:11]=1)=[O:34])([CH3:31])([CH3:32])[CH3:33]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54039568HCID 54039568, compound

Product 1

HCID 18470689HCID 18470689, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of N1-(t-butoxycarbonyl)-N2-(t-butylbenzoyl)-4-(ethoxycarbonylmethoxy)-1,2-benzenediamine (878 mg, 1.87 mmol) and CH2C12 (20 mL) was added TFA (1.5 mL, 19.5 mmol). After 12 h, the reaction was diluted with CH2Cl2 (300 ml) and washed with sat. aq. NaHCO3 (3×50 mL). The organic layer was MgSO4 dried, and concentrated. The crude material was chromatographed (65 g silica, 20% EtOAc/hexanes to 50% EtOAc/hexanes) to give the title compound (98%); IR(CHCl3): 1176, 1512, 1668, 1755, 2968 cm−1; NMR(300 MHz, DMSO-d6): 1.22 (t, 3H, J=7.2 Hz); 1.33 (s, 9H); 4.17 (q, 2H, J=7.2 Hz); 4.62 (s, 2H); 6.64 (d, 1H, J=8.7 Hz); 6.74 (d, 1H, J=8.7 Hz); 6.95 (d, 1H, J=3.0 Hz); 7.54 (d, 2H, J=8.7 Hz); 7.91 (d, 2H, J=8.1 Hz); 9.59 (s, 1H); MS(FD): 370.

Workup

  1. washwashed with sat. aq. NaHCO3 (3×50 mL)
  2. customdried
  3. concentrationconcentrated
  4. customThe crude material was chromatographed (65 g silica, 20% EtOAc/hexanes to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d9de5d43c9d04bc2b2c91a4092192a2c
Source dataset
uspto-grants-2002_07
Patent number
US06417200B1

Reaction notes

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