Methylamine → N-(Benzyloxycarbonyl)-O-methyl-L-tyrosine N-Methylamide

HRID 1589306노트

반응식

HRID 1589306 반응식
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:22]([OH:24])=O)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:26]1[C:30]2C=CC=CC=2N=N1.C1CCC(N=C=NC2CCCCC2)CC1.CN>C(Cl)Cl>[CH3:30][NH:26][C:22](=[O:24])[C@H:12]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10]

참가 물질

6

반응물 4

HCID 6329MethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 10496574(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propanoic acid

생성물 1

HCID 53688629N-(Benzyloxycarbonyl)-O-methyl-L-tyrosine N-Methylamide수율 88.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

To a stirred solution of N-(Benzyloxycarbonyl)-O-methyl-L-tyrosine (155 g, 0.471M) in dry CH2Cl2 was added 1-hydroxybenzotriazole (63.6 g, 0.471M) followed by a solution of DCC (97.2 g, 0.471M) in CH2Cl2 (100 ml) added slowly at 0° C. After warming to room temperature over 1 hr, a solution of methylamine (30 g) in CH2Cl2 (250 ml) was added dropwise to the reaction mixture which was then stirred overnight at room temperature. The reaction was then filtered, washed with saturated aqueous sodium bicarbonate (×2), dried (MgSO4) and concentrated in vacuo to give a solid. Recrystallisation from ethyl acetate/hexane gave the desired amide (142 g); m.p. 167°-170°; (Found: C, 66.72; H, 6.58; N, 8.29. C19H22N2O4 requires C, 66.65; H, 6.48; N, 8.18%) νmax (CHCl3) 3440, 1710 and 1672 cm-1 ; δ(CDCl3) 2.70 (3H, d, J=5 Hz, NCH3); 2.98 (2H, m, CH2C6H4); 3.77 (3H, s, OCH3); 4.30 (1H, dd, J=7.6 and 3 Hz, α-CH); 5.06 (2H, m, OCH2C6H5); 5.43 (1H, m, OCONH); 5.84 (1H, m, CONH); 6.80 (2H, d, J=8.6 Hz, Tyr H-3 and H-5); 7.15 (2H, d, J=8.6 Hz, Tyr H-2 and H-6); 7.32 (5H, m, C6H5); m/e 343 (100%, [m+1]+).

후처리

  1. additionadded slowly at 0° C
  2. filtrationThe reaction was then filtered
  3. washwashed with saturated aqueous sodium bicarbonate (×2)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give a solid
  7. customRecrystallisation from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-214689a4a39c44eeae7878dc8d12f6de
출처 데이터셋
uspto-grants-1986_02
특허 번호
US04568666

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