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

HRID 356079Notes

Reaction equation

HRID 356079 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]>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

7

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 1

HCID 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 CH2C12 (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 (9 H,s), 2.06-2.18 (4 H, m), 2.23-2.34 (4 H, m), 2.59 (2 H, t, J=6.8 Hz), 3.80 (3 H, s), 4.92 (1 H, m), 6.45 (1 H, s), 6.88 (1 H, d, J=7.5 Hz), 7.63 (1 H, d, J=8.6 Hz), 7.66 (1 H, s), 8.05 (1 H, 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-bac7711aacd44a7a9d96bb8a92ecf709
Source dataset
uspto-grants-1998_11
Patent number
US05834434

Reaction notes

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