4-Amino-3-methylbenzoic acid → 4-{[(Tert-butoxy)carbonyl]amino}-3-methylbenzoic acid

HRID 356078Notes

Reaction equation

HRID 356078 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11].[C:12](NC1C=CC(C(O)=O)=CC=1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]>>[C:12]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11])([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]

Participants

3

Reactant 2

HCID 755984-Amino-3-methylbenzoic acidHCID 27559314-{[(Tert-butoxy)carbonyl]amino}benzoic acid

Product 1

HCID 154320294-{[(Tert-butoxy)carbonyl]amino}-3-methylbenzoic acid

Procedure

4-amino-3-methylbenzoic acid (5 g, 33.1 mmol) was reacted according to the same procedure as N-BOC-4-aminobenzoic acid. The orange-brown solid was recrystallized from ethyl acetate and hexanes to yield 4.99 g (60%) of tan prismatic crystals. mp 180-182° C.; 1H NMR (CD3OD) 1.51 (9 H, s), 2.27 (3 H, s), 7.66 (1 H, d, J=8.1 Hz), 7.79-7.82 (2 H, m), 8.32 (1 H, s); 13C NMR (CD3OD) 17.98, 28.62, 81.47, 123.12, 127.05, 129.14, 130.65, 132.99, 142.45, 155.33, 168.70; anal calc for C13 H17NO4, C: 62.15, H: 6.82, N: 5.58; found C: 62.07, H: 6.86, N: 5.46; m/ z (EI) 251; HRMS calc. for C13H17NO4, 251.1158; found, 251.1153.

Workup

  1. customThe orange-brown solid was recrystallized from ethyl acetate and hexanes
  2. customto yield 4.99 g (60%) of tan prismatic crystals

Sources & evidence

ORD record
ord-898ec6950acc440c9e83e30990467c6f
Source dataset
uspto-grants-1998_11
Patent number
US05834434

Reaction notes

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