Dicyclohexylcarbodiimide → HCID 54118375, compound

HRID 2397562Notes

Reaction equation

HRID 2397562 reaction equation
C(O[C:6]([NH:8][C@H:9]([C:25]([OH:27])=[O:26])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)=[O:7])(C)(C)C.C(O[C:33]([NH:35][C@H:36](C(O)=O)[CH2:37][O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:34])CCC.[C:49]([O:53][C:54]([NH:56][C@H:57](C(O)=O)[CH2:58][C:59]1[C:67]2[C:62](=[CH:63][CH:64]=[CH:65][CH:66]=2)[NH:61][CH:60]=1)=[O:55])([CH3:52])([CH3:51])[CH3:50].[CH:71]1(N=C=NC2CCCCC2)CCCCC1>C(N(CC)CC)C.CO>[CH3:71][O:27][C:25](=[O:26])[C@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:15][CH:16]=1)[NH:8][C:6](=[O:7])[C@H:36]([CH2:37][O:38][CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[NH:35][C:33](=[O:34])[C@H:57]([CH2:58][C:59]1[C:67]2[C:62](=[CH:63][CH:64]=[CH:65][CH:66]=2)[NH:61][CH:60]=1)[NH:56][C:54]([O:53][C:49]([CH3:51])([CH3:52])[CH3:50])=[O:55]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 83169N-tert-Butoxycarbonyl-L-tryptophanHCID 98763O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosineHCID 53933599HCID 53933599, compound

Product 1

HCID 54118375HCID 54118375, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

Nα-t-Butoxycarbonyl-L-tryptophyl-O-benzyl-L-seryl-O-benzyl-L-tyrosine methyl ester is prepared from 40 g. (29 mmol) of Nα-t-butoxycarbonyl-O-benzyl-L-tyrosine resin by successive couplings according to the solid-phase procedure with (1) 10 g. of Nα-butoxycarbonyl-O-benzyl-L-serine (33 mmol) and 7 g. (34 mmol) of dicyclohexycarbodiimide, (2) 10 g. (33 mmol) of Nα-t-butoxycarbonyl-L-tryptophan and 7 g. of dicyclohexylcarbodiimide. The resulting resin, 44 g., is converted to the methyl ester by stirring it overnight at room temperature with 300 ml. of methanol and 30 ml. of triethylamine. The mixture is filtered and the solvent evaporated. The residual oil solidifies and is crystallized from isopropanol to yield 10 g. of white solid, m.p. 130°-131° C.

Workup

  1. filtrationThe mixture is filtered
  2. customthe solvent evaporated
  3. customThe residual oil solidifies and is crystallized from isopropanol
  4. customto yield 10 g

Sources & evidence

ORD record
ord-f4b0e95672be40b6a6febb9e3f073a75
Source dataset
uspto-grants-1977_05
Patent number
US04022761

Reaction notes

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