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Triethylamine → N-BOC-S-trityl-cysteine 4-amino-3-methoxybenzoyl methionine methyl ester

HRID 1739135
ノート
印刷プレビュー

反応式

HRID 1739135 の反応式
[C:1]([NH:8][C@H:9]([C:31]([OH:33])=[O:32])[CH2:10][S:11][C:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN(CC)CC.Cl.[CH3:42][O:43][C:44](=[O:62])[C@H:45]([CH2:58][CH2:59][S:60][CH3:61])[NH:46][C:47](=[O:57])[C:48]1[CH:53]=[CH:52][C:51]([NH2:54])=[C:50]([O:55][CH3:56])[CH:49]=1.C(N[C@H](C(O)=O)CSC(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(OC(C)(C)C)=O.COC(=O)[C@H](CCSC)NC(=O)C1C=CC(N)=CC=1>C1COCC1.C(Cl)Cl>[C:1]([NH:8][C@H:9]([C:31]([OH:33])=[O:32])[CH2:10][S:11][C:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:42][O:43][C:44](=[O:62])[C@H:45]([CH2:58][CH2:59][S:60][CH3:61])[NH:46][C:47](=[O:57])[C:48]1[CH:53]=[CH:52][C:51]([NH2:54])=[C:50]([O:55][CH3:56])[CH:49]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471Triethylamine2 回HCID 11167161N-((1,1-Dimethylethoxy)carbonyl)-S-(triphenylmethyl)-L-cysteineHCID 67565269N-BOC-S-trityl-cysteine 4-aminobenzoyl methionine methyl esterHCID 67566236HCl 4-amino-3-methoxybenzoyl methionine methyl ester

生成物 1

HCID 67601241N-BOC-S-trityl-cysteine 4-amino-3-methoxybenzoyl methionine methyl ester
収率 15.2%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

N-BOC-S-trityl-cysteine (0.76 g, 1.74 mmol) in dry THF (27.5 ml) was reacted with Et3N (0.24 ml), IBCF (0.23 ml, 1.74 mmol) at -10° C. as described above. HCl-4-amino-3-methoxybenzoyl methionine methyl ester (0.55 g, 1.58 mmol) in dry CH2Cl2 (8.7 ml) with Et3N (0.30 ml) was added to the mixture and was allowed to stir overnight under nitrogen. It was worked up as described for N-BOC-S-trityl-cysteine-4-aminobenzoyl methionine methyl ester in Example 1, and the crude material was chromatographed on silica gel using a 2:1 mixture of hexanes and ethyl acetate to give 0.18 g (15.2%) of pure product. 1H NMR (CDCl3) 1.45 (9H, s), 2.05-2.33 (5H, m), 2.57-2.65 (2H, m), 2.68-2.72 (1H, m), 2.75-2.96 (1H, m), 3.78 (3H, s), 3.84 (3H, s), 4.90-5.00 (1H, m), 5.03-5.18 (1H, m), 7.17-7.48 (17H, m), 8.30-8.38 (1H, m), 8.65 (1H, br s).

後処理

  1. customthe crude material was chromatographed on silica gel using
  2. additiona 2:1 mixture of hexanes and ethyl acetate

出典と根拠

ORDレコード
ord-f31e4982a1604037b237fb8d839e0176
出典データセット
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05965539

反応ノート

読み込み中…

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