Dichloromethane → N-BOC-S-trityl-cysteine 4-amino-2-(3,5-dimethylphenyl)benzoyl methionine methyl ester

HRID 356094ノート

反応式

HRID 356094 の反応式
[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:23][CH2:24][S:25][CH3:26])[NH:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[CH:15]=1.C(Cl)Cl.CCN(CC)CC.[C:38]([NH:45][C@H:46]([C:68]([OH:70])=[O:69])[CH2:47][S:48][C:49]([C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=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:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39].COC(=O)[C@H](CCSC)NC(=O)C1C=CC(N)=CC=1>C1COCC1>[C:38]([NH:45][C@H:46]([C:68]([OH:70])=[O:69])[CH2:47][S:48][C:49]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)([C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39].[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:23][CH2:24][S:25][CH3:26])[NH:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[C:14]1[CH:15]=[C:16]([CH3:21])[CH:17]=[C:18]([CH3:20])[CH:19]=1

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 186667574-Amino-2-(3,5-dimethylphenyl)benzoyl methionine methyl esterHCID 67565269N-BOC-S-trityl-cysteine 4-aminobenzoyl methionine methyl ester

生成物 1

HCID 67601032N-BOC-S-trityl-cysteine 4-amino-2-(3,5-dimethylphenyl)benzoyl methionine methyl ester収率 56%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

4-amino-2-(3,5-dimethylphenyl)benzoyl methionine methyl ester (0.10 g, 0.26 mmol) was dissolved into dry CH2Cl2 (1.4 ml) and it was allowed to stand. In another flask, N-BOC-S-trityl-Cys (0.12 g, 0.26 mmol) was dissolved into THF (4.4 ml) and was reacted with IBCF (0.03 ml) and Et3N (0.04 ml) as described above. The product was worked up as described for N-BOC-S-trityl-cysteine-4-aminobenzoyl methionine methyl ester in Example 1 and chromatographed on silica gel using a 1:1 hexanes and ethyl acetate elution mixture to give 0.12 g (56.0%) of pure material. 1H NMR (CDCl3) 1.33 (9 H, ), 1. 61-1.68 (1 H, m), 1.73-1.91 (4 H, m) , 1.96 (2 H, t, J=7.6 Hz) , 2.24 (6 H, s), 2.57-2.64 (2 H, m), 3.57 (3 H, s), 4.00 (1 H, br s), 4.54-4.58 (1 H, m), 5.84 (1 H, d, J=7.8 Hz), 5.97 (1 H, br d), 6.90 (1 H, s), 6.92 (2 H, s), 7.18-7.22 (9 H, m), 7.27-7.40 (7 H, m), 7.55 (1 H, m), 7.61 (1 H, m), 8.58 (1 H, br s); 13C NMR (CDCl3) 15.11, 21.20, 27.79, 29.25, 31.28, 51.70, 52.28, 54.08, 60 .32, 71.45, 80.75, 118.01, 120.80, 126.38, 126.82, 127.98, 129.41, 129.87, 130.22, 138.11, 139.18, 139.79, 141.06, 144.17, 168.38, 169.04, 171.82.

後処理

  1. customchromatographed on silica gel using
  2. washa 1:1 hexanes and ethyl acetate elution mixture

出典と根拠

ORDレコード
ord-09c98fde26854eb0b2768a1ed17ff7ad
出典データセット
uspto-grants-1998_11
特許番号
US05834434

反応ノート

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