1,2-Dichloroethane → Ac-Pro-Leu-Gly-S-Leu-Leu-Gly-OC2H5

HRID 1982357Notes

Reaction equation

HRID 1982357 reaction equation
[N:1]1([C:21]([CH3:23])=[O:22])[CH2:20][CH2:19][CH2:18][C@H:2]1[C:3]([NH:5][C@H:6]([C:11]([NH:13][CH2:14][C:15]([OH:17])=O)=[O:12])[CH2:7][CH:8]([CH3:10])[CH3:9])=[O:4].[SH:24][NH:25][C@H:26]([C:31]([NH:33][C@H:34]([C:39]([NH:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])=[O:40])[CH2:35][CH:36]([CH3:38])[CH3:37])=[O:32])[CH2:27][CH:28]([CH3:30])[CH3:29].C(Cl)CCl>CN(C)C=O>[N:1]1([C:21]([CH3:23])=[O:22])[CH2:20][CH2:19][CH2:18][C@H:2]1[C:3]([NH:5][C@H:6]([C:11]([NH:13][CH2:14][C:15]([S:24][NH:25][C@H:26]([C:31]([NH:33][C@H:34]([C:39]([NH:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])=[O:40])[CH2:35][CH:36]([CH3:38])[CH3:37])=[O:32])[CH2:27][CH:28]([CH3:30])[CH3:29])=[O:17])=[O:12])[CH2:7][CH:8]([CH3:9])[CH3:10])=[O:4]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 7408272Ac-Pro-Leu-Gly-OHHCID 131714519HS-Leu-Leu-Gly-OC2H5

Product 1

HCID 91977864Ac-Pro-Leu-Gly-S-Leu-Leu-Gly-OC2H5Yield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Ac-Pro-Leu-Gly-OH (0.7 g, 2.1 mmol), HS-Leu-Leu-Gly-OC2H5 (0.6 g, 1.7 mmol) and HBT (0.26 g, 1.7 mmol) in 15 ml dimethylformamide was added EDC (0.4 g, 2.1 mmol). The solution was stirred at room temperature overnight. The solvent was removed in vacuo and the residue partitioned between salt water and ethyl acetate. The ethyl acetate layer was washed consecutively with dilute sodium bicarbonate in salt (NaCl) water, dilute hydrochloric acid in salt water, salt water, 1.0 mM cupric sulfate in salt water (to remove any mercapto products) and finally salt water. The ethyl acetate was dried over magnesium sulfate. The magnesium sulfate was removed by filtration and the filtrate concentrated in vacuo, yielding 0.8 g (73%) glassy residue of crude thiopeptolide product. A 100 mg sample of this crude product was purified by low pressure C18 column chromatography. The purified thiopeptolide, had an acceptable amino acid analysis, a consistent mass spectrum and a single peak on HPLC analysis. Anal. Calcd. for

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between salt water and ethyl acetate
  3. washThe ethyl acetate layer was washed consecutively with dilute sodium bicarbonate in salt (NaCl) water, dilute hydrochloric acid in salt water, salt water, 1.0 mM cupric sulfate in salt water (
  4. customto remove any mercapto products) and finally salt water
  5. dry with materialThe ethyl acetate was dried over magnesium sulfate
  6. customThe magnesium sulfate was removed by filtration
  7. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-8fa166e3b761425da88ac76728f44136
Source dataset
uspto-grants-1986_06
Patent number
US04596675

Reaction notes

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