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

HRID 356079
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HRID 356079 반응식
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]
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참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-bac7711aacd44a7a9d96bb8a92ecf709
출처 데이터셋
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05834434

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