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

HRID 356096Notes

Reaction equation

HRID 356096 reaction equation
C([NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19]([OH:21])=O)=[CH:11][CH:10]=1)(OC(C)(C)C)=O.Cl.COC(=O)[C@H](CCSC)N.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:54][O:55][C:56](=[O:79])[C@H:57]([CH2:75][CH2:76][S:77][CH3:78])[N:58](C(=O)C1C=CC(N)=CC=1)[C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60]>C(Cl)Cl.CCN(CC)CC>[CH3:54][O:55][C:56](=[O:79])[C@H:57]([CH2:75][CH2:76][S:77][CH3:78])[N:58]([C:19]([C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([NH2:8])=[CH:10][CH:11]=1)=[O:21])[C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 234361804-((tert-Butoxycarbonyl)amino)-1-naphthoic acidHCID 67564255N-BOC-4-aminobenzoyl methionine methyl ester

Product 1

HCID 67565447N-BOC-4-amino-1-naphthoyl methionine methyl esterYield 63.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

N-BOC-4-amino-1-naphthoic acid (0.46 g, 1.60 mmol), methionine methyl ester hydrochloride (0.35 g, 1.76 mmol), EDCI (0.43 g, 1.76 mmol), HOBT (0.24 g, 1.76 mmol) and Et3N (0.27 ml) in CH2Cl2 (6.4 ml) were reacted as described for N-BOC-4-aminobenzoyl methionine methyl ester in Example 1. After workup and recrystallization from ethyl acetate and hexanes, 0.44 g (63.6%) of pale pink crystals were obtained. mp 131°-132° C.; 1H NMR (CDCl3) 1.57 (9 H, s), 2.11-2.21 (4 H, m), 2.29-2.41 (1 H, m), 2.65 (2 H, t, J=7.1 Hz), 3.83 (3 H, s), 4.99-5.06 (1 H, m), 6.68 (1 H, d, J=8.0), 7.02 (1 H, s), 7.56-7.59 (2 H, m), 7.69 (1 H, d, J=7.9 Hz), 7.87-7.90 (1 H, m), 8.02 (1 H, d, J=7.9 Hz), 8.44-8.48 (1 H, m); 13C NMR (CDCl3) 15.56, 28.31, 30.19, 31.65, 52.06, 52.64, 81.17, 115.82, 120.18, 125.79, 126.37, 126.53, 127.18, 131.02, 135.65, 152.93, 169.04, 172.40; HRMS calc. for C22 H28N2O5S, 432.1719; found 432.1702; m/z (FAB) 433 (M+1).

Workup

  1. customAfter workup and recrystallization from ethyl acetate and hexanes

Sources & evidence

ORD record
ord-3ddb407ce3c54477ade46e84c67709ed
Source dataset
uspto-grants-1998_11
Patent number
US05834434

Reaction notes

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