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

HRID 259006

반응식

HRID 259006 반응식
[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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-62a0526bc4bc4866a106d1b83a75f9e4
출처 데이터셋
uspto-grants-1977_07
특허 번호
US04035348

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