1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-BOC-4-amino-3-methoxybenzoyl methionine methyl ester

HRID 1739133Notes

Reaction equation

HRID 1739133 reaction equation
C([NH:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][C:10]=1[O:18][CH3:19])(OC(C)(C)C)=O.Cl.COC(=O)[C@H](CCSC)N.CCN=C=NCCCN(C)C.[CH3:42][O:43][C:44](=[O:67])[C@H:45]([CH2:63][CH2:64][S:65][CH3:66])[N:46](C(=O)C1C=CC(N)=CC=1)[C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48]>>[CH3:42][O:43][C:44](=[O:67])[C@H:45]([CH2:63][CH2:64][S:65][CH3:66])[N:46]([C:13](=[O:15])[C:12]1[CH:16]=[CH:17][C:9]([NH2:8])=[C:10]([O:18][CH3:19])[CH:11]=1)[C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48]

Participants

5

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 154320334-((tert-Butoxycarbonyl)amino)-3-methoxybenzoic acidHCID 67564255N-BOC-4-aminobenzoyl methionine methyl ester

Product 1

HCID 67566384N-BOC-4-amino-3-methoxybenzoyl methionine methyl esterYield 57.2%

Procedure

N-BOC-4-amino-3-methoxybenzoic acid (0.35 g, 1.31 mmol) was reacted with methionine methyl ester hydrochloride (0.9 g, 1.43 mmol) using EDCI as in N-BOC-4-aminobenzoyl methionine methyl ester. After recrystallization from ethyl acetate and hexanes, 0.36 g (57.2%) of pure product was obtained. mp 163-165° C.; 1H NMR (CDCl3) 1.53 (9H, s), 2.09-2.18 (4H, m), 2.23-2.35 (1H, m), 2.60 (2H, t, J=6.9 Hz), 3.80 (3H, s), 3.93 (3H, s), 4.92 (1H, br s), 6.93 (1H, d, J=7.6 Hz), 7.25 (1H, m), 7.31 (1H, d, J=10.2 Hz), 7.44(1H, s), 8.15(1H, d, J=8.5 Hz); 13C NMR (CDCl3) 15.47, 28.23, 30.09, 31.48, 52.06, 52.54, 55.81, 80.82, 98.06, 109.38, 116.66, 119.31, 131.52, 147.23, 152.31, 166.57, 172.58; m/z (FAB) 413 (M+1).

Workup

  1. customAfter recrystallization from ethyl acetate and hexanes

Sources & evidence

ORD record
ord-8a1e5895dd594a31aed1465060ff46f3
Source dataset
uspto-grants-1999_10
Patent number
US05965539

Reaction notes

Loading…