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

HRID 259006

Reaction equation

HRID 259006 reaction equation
[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]

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-62a0526bc4bc4866a106d1b83a75f9e4
Source dataset
uspto-grants-1977_07
Patent number
US04035348

Linked notes

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