1,2-Dichloroethane → HCID 508625, compound

HRID 397794Notes

Reaction equation

HRID 397794 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C@H:16]([C:45]([OH:47])=[O:46])[CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([C@@H:24]([NH:35][S:36]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)(=[O:38])=[O:37])[CH2:25][C:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[NH:28][CH:27]=2)=[O:23])[CH2:12][CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH:48][CH2:49][CH:50]([CH2:52]O)[OH:51].C(Cl)CCl>CN(C=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([C@H:16]([C:45]([O:47][CH2:52][CH:50]([OH:51])[CH2:49][OH:48])=[O:46])[CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([C@@H:24]([NH:35][S:36]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)(=[O:37])=[O:38])[CH2:25][CH:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28]=[CH:27]2)=[O:23])[CH2:12][CH:13]([CH3:15])[CH3:14])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 753GlycerolHCID 508529HCID 508529, compound

Product 1

HCID 508625HCID 508625, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

Nα-isobutyl-Nα-(4-methylbenzenesulfonyl)-Nε-(N′α-benzenesulfonyl-L-tryptophanyl)-L-lysine (170 mg, 0.25 mmol) dissolved in a solution of DMF (1 mL) was treated with glycerol (100 mL, 1.37 mmol) and EDC (100 mg, 0.5 mmol) and stirred overnight. Then, the solution was poured in 5% citric acid and extracted with EtOAc. The solvent was evaporated and the residue purified by preparative HPLC to give 150 mg (79%) of the final product.

Workup

  1. extractionextracted with EtOAc
  2. customThe solvent was evaporated
  3. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-5dc2c131b3a947a58c5fbf7af4b1f5cb
Source dataset
uspto-grants-2003_08
Patent number
US06610689B2

Reaction notes

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