N-Acetyl-tyrosinyl-valinyl-4-allyloxyproline → N-(N-Acetyl-tyrosinyl-valinyl-(4(R)-allyloxyprolinyl))-3(S)-amino-4-oxobutanoic acid tert-butyl ester semicarbazone

HRID 2229944노트

반응식

HRID 2229944 반응식
[C:1]([NH:4][C@H:5]([C:14]([NH:16][C@H:17]([C:21]([N:23]1[CH2:30][CH:29]([O:31][CH2:32][CH:33]=[CH2:34])[CH2:28][C@H:24]1[C:25](O)=[O:26])=[O:22])[CH:18]([CH3:20])[CH3:19])=[O:15])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)(=[O:3])[CH3:2].[C:35]([O:39][C:40](=[N:46][NH:47][C:48]([NH2:50])=[O:49])[CH2:41][CH:42]([NH2:45])[CH:43]=[O:44])([CH3:38])([CH3:37])[CH3:36]>>[C:35]([O:39][C:40](=[N:46][NH:47][C:48]([NH2:50])=[O:49])[CH2:41][C@H:42]([NH:45][C:25](=[O:26])[C@@H:24]1[CH2:28][C@@H:29]([O:31][CH2:32][CH:33]=[CH2:34])[CH2:30][N:23]1[C:21](=[O:22])[C@H:17]([CH:18]([CH3:19])[CH3:20])[NH:16][C:14](=[O:15])[C@H:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1)[NH:4][C:1](=[O:3])[CH3:2])[CH:43]=[O:44])([CH3:38])([CH3:36])[CH3:37]

참가 물질

3

반응물 2

HCID 22881982N-Acetyl-tyrosinyl-valinyl-4-allyloxyprolineHCID 539854003-Amino-4-oxobutyric acid tert-butyl ester semicarbazone

생성물 1

HCID 86671131N-(N-Acetyl-tyrosinyl-valinyl-(4(R)-allyloxyprolinyl))-3(S)-amino-4-oxobutanoic acid tert-butyl ester semicarbazone수율 20%

실험 절차

N-Acetyl-tyrosinyl-valinyl-(4-allyloxyproline) methyl ester (770 mg, 1.57 mmol) was dissolved in 20 ml of tetrahydrofuran and 4 ml of methanol. Lithium hydroxide (145 mg, 3.46 mmol) was added to the mixture and stirred at room temperature. After two hours, 1 ml of 10% hydrogen chloride was added and the mixture evaporated in vacuo to give a solid residue then partitioned between Sml of water and 50 ml of ethyl acetate and the organic layer separated and evaporated in vacuo to give 430 mg of the acid that waa used immediately in the next step. N-Acetyl-tyrosinyl-valinyl-4-allyloxyproline (420 mg, 0.88 mmol) and 3-amino-4-oxobutyric acid tert-butyl ester semicarbazone (184 mg, 0.8 mol, Graybill et al., Int. J. Protein Res., 44, pp. 173-82 (1994)) to give 100 mg (20%) of the title compound as a white amorphous solid: 1H NMR (CD3OD) δ7.24-7.2 (1H, m), 7.04-6.97 (2H, d), 6.73-6.65 (2H, d), 5.98-5.86 (1H, m), 5.35-5.24 (1H, d), 5.17-5.12 (1H, m), 4.12-3.98 (2H, m), 3.72-3.67 (1H, m), 2.98-2.92 (3H, m), 2.38-2.32 (1H, m), 2.1-2.02 (2H, m), 1.92 (3H, s), 0.98-0.89 (6H, 2×d).

출처 및 근거

ORD 기록
ord-aba77bd0bfac41f28e98996ce7ea90ff
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06420522B1

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