2486-69-3 → 4-((tert-Butoxycarbonyl)amino)-3-methoxybenzoic acid

HRID 1532809Notes

Reaction equation

HRID 1532809 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:11][CH3:12].[C:13](NC1C=CC(C(O)=O)=CC=1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>>[C:13]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:11][CH3:12])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Participants

3

Reactant 2

HCID 2880572486-69-3HCID 27559314-{[(Tert-butoxy)carbonyl]amino}benzoic acid

Product 1

HCID 154320334-((tert-Butoxycarbonyl)amino)-3-methoxybenzoic acid

Procedure

4-Amino-3-methoxybenzoic acid (1 g, 5.98 mmol) was reacted according to the same procedure as that used in the process for preparing N-BOC-4-aminobenzoic acid. The resulting solid was recrystallized from ethyl acetate and hexanes to provide the desired product (1.5 g) as tan crystals: m.p. 176-178° C.; 1H NMR (CD3OD) d 1.52 (9H, s), 3.92 (3H, s), 7.56 (1H, s), 7.62 (1H, d, J=8.4 Hz), 7.96 (1H, s), 8.03 (1H, d, J=8.4 Hz); 13C NMR (CD3OD) d 28.53, 56.35, 81.78, 112.01, 118.58, 124.20, 125.76, 133.84, 149.04, 154.20, 169.60; HRMS Calc. for C13H17NO5, 267.1107; Found, 267.1103.

Workup

  1. customThe resulting solid was recrystallized from ethyl acetate and hexanes

Sources & evidence

ORD record
ord-bdff42dc66c8484b9f710aa49f6efb97
Source dataset
uspto-grants-2001_03
Patent number
US06204293B1

Reaction notes

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