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

HRID 1739131Notes

Reaction equation

HRID 1739131 reaction equation
C([NH:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][C:10]=1[CH3:18])(OC(C)(C)C)=O.Cl.COC(=O)[C@H](CCSC)N.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:51][O:52][C:53](=[O:76])[C@H:54]([CH2:72][CH2:73][S:74][CH3:75])[N:55](C(=O)C1C=CC(N)=CC=1)[C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57]>C(Cl)Cl.CCN(CC)CC>[CH3:51][O:52][C:53](=[O:76])[C@H:54]([CH2:72][CH2:73][S:74][CH3:75])[N:55]([C:13](=[O:15])[C:12]1[CH:16]=[CH:17][C:9]([NH2:8])=[C:10]([CH3:18])[CH:11]=1)[C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 154320294-{[(Tert-butoxy)carbonyl]amino}-3-methylbenzoic acidHCID 67564255N-BOC-4-aminobenzoyl methionine methyl ester

Product 1

HCID 67566381N-BOC-4-amino-3-methylbenzoyl methionine methyl esterYield 85.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

N-BOC-4-amino-3-methylbenzoic acid (2.00 g, 7.96 mmol) was reacted with methionine methyl ester hydrochloride (1.75 g, 8.76 mmol), EDCI (1.68 g, 8.76 mmol), HOBT (1.18 g, 8.76 mmol) and Et3N (1.4 ml) in dry CH2Cl2 (31.8 ml) according to the procedure described for N-BOC-4-aminobenzoyl methionine methyl ester in Example 1. The crude material was recrystallized from ethyl acetate and hexanes to yield 2.61 g (85.7%) of pure product. mp 163-165° C.; 1H NMR (CDCl3) 1.54 (9H, s), 2.06-2.18 (4H, m), 2.23-2.34 (4H, m), 2.59 (2H, t, J=6.8 Hz), 3.80 (3H, s), 4.92 (1H, m), 6.45 (1H, s), 6.88 (1H, d, J=7.5 Hz), 7.63 (1H, d, J=8.6 Hz), 7.66 (1H, s), 8.05 (1H, d, J=8.6); 13C NMR (CDCl3) 15.47, 17.61, 28.22, 30.03, 31.55, 51.93, 52.57, 81.04, 118.73, 125.62, 127.66, 129.54, 139.89, 152.34, 166.58, 172.66.

Workup

  1. customThe crude material was recrystallized from ethyl acetate and hexanes

Sources & evidence

ORD record
ord-485f92186b3d44d1b458569598929428
Source dataset
uspto-grants-1999_10
Patent number
US05965539

Reaction notes

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