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 2229944ノート

反応式

HRID 2229944 の反応式
[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]

参加物

3

反応物 2

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

生成物 1

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

実験手順

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).

出典と根拠

ORDレコード
ord-aba77bd0bfac41f28e98996ce7ea90ff
出典データセット
uspto-grants-2002_07
特許番号
US06420522B1

反応ノート

読み込み中…