Dicyclohexylcarbodiimide → Nalpha-Benzyloxycarbonyl-L-tryptophyl-O-benzyl-D-tyrosyl-O-benzyl-L-seryl-D-alanine methyl ester

HRID 259006

反応式

HRID 259006 の反応式
[CH3:1][O:2][C:3](=[O:60])[C@@H:4]([CH3:59])[NH:5][C:6](=[O:58])[C@H:7]([CH2:49][O:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[NH:8][C:9](=[O:48])[C@@H:10]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[CH:36][CH:35]=1)[NH:11][C:12](=[O:32])[C@H:13]([CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)[NH:14][C:15]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:16].[CH2:61](OC(N[C@H](C(O)=O)CC1C2C(=CC=CC=2)NC=1)=O)[C:62]1C=CC=C[CH:63]=1.C1(N=C=NC2CCCCC2)CCCCC1.C(ON[C@H](C(N[C@@H](C(N[C@H](C(N[C@@H](C(O)=O)C)=O)COCC1C=CC=CC=1)=O)CC1C=CC(OCC2C=CC=CC=2)=CC=1)=O)C(=C=O)C1C2C(=CC=CC=2)NC=1)C1C=CC=CC=1>CN(C)C=O.CO.C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:60])[C@@H:4]([CH3:59])[NH:5][C:6](=[O:58])[C@H:7]([CH2:49][O:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[NH:8][C:9](=[O:48])[C@@H:10]([CH2:33][C:34]1[CH:35]=[CH:36][C:37]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[CH:38][CH:39]=1)[NH:11][C:12](=[O:32])[C@H:13]([CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)[NH:14][C:15]([O:17][CH2:18][C:19]1[CH:63]=[CH:62][CH:61]=[CH:21][CH:20]=1)=[O:16]

参加物

8

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 101176benzyloxycarbonyl-L-tryptophanHCID 54357206Nalpha-Butoxycarbonyl-L-tryptophyl-O-benzyl-D-tyrosyl-O-benzyl-L-seryl-D-alanine methyl esterHCID 86734937Nalpha-benzyloxy-carbonyl-L-tryptophyl-O-benzyl-D-tyrosyl-O-benzyl-L-seryl-D-alanine

生成物 1

HCID 54242907Nalpha-Benzyloxycarbonyl-L-tryptophyl-O-benzyl-D-tyrosyl-O-benzyl-L-seryl-D-alanine methyl ester

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

Nα-t-Butoxycarbonyl-O-benzyl-O-tyrosyl-O-benzyl-L-seryl-D-alanine resin (Example 11), 6.4 g., 5.1 mmol, is coupled with 2.23 g., 6.3 mmol, of Nα-benzyloxycarbonyl-L-tryptophan and 1.3 g., 6.3 mmol, of dicyclohexylcarbodiimide according to the general procedure of Example 1. The resulting Nα-benzyloxy-carbonyl-L-tryptophyl-O-benzyl-D-tyrosyl-O-benzyl-L-seryl-D-alanine resin is mixed with 20 ml. of triethylamine, 150 ml. of methanol and 50 ml. of dimethylformamide and let stand overnight. After filtration and evaporation, the crude product is triturated with either-petroleum ether and crystallized from isopropanol; 1.75 g.; [α]D 23 -5° (c. 1.01, DMF).

後処理

  1. filtrationAfter filtration and evaporation
  2. customthe crude product is triturated with either-petroleum ether
  3. customcrystallized from isopropanol

出典と根拠

ORDレコード
ord-62a0526bc4bc4866a106d1b83a75f9e4
出典データセット
uspto-grants-1977_07
特許番号
US04035348

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