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Hydrochloric Acid → N-BOC-S-trityl-cysteine 4-amino-1-naphthoyl methionine methyl ester

HRID 356097
ノート
印刷プレビュー

反応式

HRID 356097 の反応式
CCN(CC)CC.Cl.[CH3:9][O:10][C:11](=[O:31])[C@H:12]([CH2:27][CH2:28][S:29][CH3:30])[NH:13][C:14]([C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([NH2:26])=[CH:18][CH:17]=1)=[O:15].[C:32]([NH:39][C@H:40]([C:62]([OH:64])=[O:63])[CH2:41][S:42][C:43]([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].COC(=O)[C@H](CCSC)NC(=O)C1C=CC(N)=CC=1>C1COCC1.C(Cl)Cl>[C:32]([NH:39][C@H:40]([C:62]([OH:64])=[O:63])[CH2:41][S:42][C:43]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].[CH3:9][O:10][C:11](=[O:31])[C@H:12]([CH2:27][CH2:28][S:29][CH3:30])[NH:13][C:14]([C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([NH2:26])=[CH:18][CH:17]=1)=[O:15]
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 313Hydrochloric AcidHCID 8471TriethylamineHCID 537463294-Amino-1-naphthoyl methionine methyl esterHCID 67565269N-BOC-S-trityl-cysteine 4-aminobenzoyl methionine methyl ester

生成物 1

HCID 67566653N-BOC-S-trityl-cysteine 4-amino-1-naphthoyl methionine methyl ester収率 37.5%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

N-BOC-S-trityl-Cys (0.31 g, 0.67 mmol) in dry THF (11.2 ml) was reacted with Et3N (0.10 ml) and IBCF (0.10 ml, 0.74 mmol) at -10° C. as described above. HCl.4-amino-1-naphthoyl methionine methyl ester (0.25 g, 0.67 mmol) in dry CH2Cl2 (3.5 ml) was added and the mixture was stirred overnight under nitrogen. The mixture 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 0.20g (37.5 %) of pure product. 1H NMR (CDCl3) 1.48 (9 H, s), 2.10-2.20 (4 H, m), 2.30-2.37 (1 H, m), 2.63 (2 H, t, J=7.4), 2.74 (1 H, J=12.9 Hz, J=5.3 Hz), 2.90 (1 H, J=12.9 Hz, 6.2 Hz), 3.81 (3 H, s), 4.96-5.03 (2 H, m), 6.77 (1 H, d, J=8.0 Hz), 7.18-7.33 (11 H, m), 7.44-7.56 (7 H, m), 7.60 (1 H, d, J=7.7 Hz), 7.88 (1 H, d, J=8.0 Hz), 8.00 (1 H, d, J=7.1 Hz), 8.37 (1 H, d, J=8.4 Hz), 8.94 (1 H, br s); 13C NMR (CDCl3) 15.23, 26.52, 31.41, 31.50, 52.98, 53.31, 56.79, 68.15, 122.52, 123.54, 126.16, 126.99, 128.03, 128.39, 129.52, 132.30, 134.04, 135.24, 168.08, 172.38, 173.94.

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-3b41ded45bcb441c943ff4ca83af8f85
出典データセット
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05834434

反応ノート

読み込み中…

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