Dicyclohexylcarbodiimide → HCID 131713589, compound

HRID 1462854Notes

Reaction equation

HRID 1462854 reaction equation
[NH:1]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:2]([C:12]([OH:14])=O)[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH2:22][C@H:23]([C:40]([NH:42][C@H:43]([C:59]([O:61][CH2:62][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)=[O:60])[CH2:44][CH2:45][CH2:46][CH2:47][NH:48][C:49]([O:51][CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)=[O:50])=[O:41])[CH2:24][C:25]1[N:29]=[CH:28][N:27]([S:30]([C:33]2[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=2)(=[O:32])=[O:31])[CH:26]=1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[NH:1]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:2]([C:12]([NH:22][C@H:23]([C:40]([NH:42][C@H:43]([C:59]([O:61][CH2:62][C:63]1[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=1)=[O:60])[CH2:44][CH2:45][CH2:46][CH2:47][NH:48][C:49]([O:51][CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)=[O:50])=[O:41])[CH2:24][C:25]1[N:29]=[CH:28][N:27]([S:30]([C:33]2[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=2)(=[O:32])=[O:31])[CH:26]=1)=[O:14])[CH2:3][O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 131713587HCID 131713587, compound

Product 1

HCID 131713589HCID 131713589, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

A mixture of 1.67 g of Boc-Ser(Bzl), 3.75 g of His(Tos)-Lys(Z)-OBzl and 13.2 ml of methylene chloride was cooled to -15° C., and 1.28 g of DCC was added to the mixture under stirring. Two hours later, the mixture was further stirred at room temperature for 2 hours. Insoluble matters were filtered off and washed with ethyl acetate. The filtrate and the washing were combined and washed with aqueous citric acid, saturated saline and sodium bicarbonate aqueous solution, dried over sodium sulfate anhydride. Then, the solvent was distilled off. The resultant oil residue was crystallized by adding ether to obtain 4.2 g of Boc-Ser(Bzl)-His(Tos)-Lys(Z)-OBzl.

Workup

  1. stirringTwo hours later, the mixture was further stirred at room temperature for 2 hours
  2. filtrationInsoluble matters were filtered off
  3. washwashed with ethyl acetate
  4. washwashed with aqueous citric acid, saturated saline and sodium bicarbonate aqueous solution
  5. dry with materialdried over sodium sulfate anhydride
  6. distillationThen, the solvent was distilled off
  7. customThe resultant oil residue was crystallized
  8. additionby adding ether

Sources & evidence

ORD record
ord-1742ae709a9d40a09da391cd7876296d
Source dataset
uspto-grants-1984_07
Patent number
US04461724

Reaction notes

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