Hydrochloric Acid → HCID 86751036, compound

HRID 2287498Notes

Reaction equation

HRID 2287498 reaction equation
[CH2:1]([O:8][C:9]([C@@H:11]1[C@H:15]([C:16]([OH:18])=[O:17])[CH2:14][C:13](=[O:19])[O:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(N=C=NCCCN(C)C)C.[C:32](O)([CH3:35])([CH3:34])[CH3:33].Cl>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[O:19]=[C:13]1[O:12][C@H:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[C@@H:15]([C:16]([O:18][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:17])[CH2:14]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6386tert-ButanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57182103HCID 57182103, compound

Product 1

HCID 86751036HCID 86751036, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

To 7.93 g of (2S,3R)-2-benzyloxycarbonyl-5-oxotetrahydrofuran-3-carboxylic acid in 75 ml of chloroform, 5.5 g of 4-dimethylaminopyridine, 8.6 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 5.7 ml of tert-butyl alcohol were successively added, and the resulting reaction solution was stirred at room temperature for 60 hours. The reaction solution was poured into 1N hydrochloric acid cooled with ice and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, the desiccant was filtered off, the solvent was evaporated in vacuo, and the residue was purified by silica gel column chromatography [hexane/ethyl acetate=5/1] to give 6.48 g of the title compound as a white solid.

Workup

  1. customthe resulting reaction solution
  2. temperaturecooled with ice
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationthe desiccant was filtered off
  6. customthe solvent was evaporated in vacuo
  7. customthe residue was purified by silica gel column chromatography [hexane/ethyl acetate=5/1]

Sources & evidence

ORD record
ord-f17f1caa0783404aafaa1451fc8c33a0
Source dataset
uspto-grants-2000_07
Patent number
US06083985

Reaction notes

Loading…