1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 18337567, compound

HRID 2298013Notes

Reaction equation

HRID 2298013 reaction equation
C1OC2C=CC(C[O:7][C:8](=O)[C@H:9]([N:20]([CH2:35][C:36]3[CH:41]=[CH:40][C:39]4[O:42][CH2:43][O:44][C:38]=4[CH:37]=3)[S:21]([C:24]3[C:29]([CH3:30])=[CH:28][C:27]([O:31][CH3:32])=[C:26]([CH3:33])[C:25]=3[CH3:34])(=[O:23])=[O:22])[C@@H:10]([O:12][Si](CC)(CC)CC)[CH3:11])=CC=2O1.[CH2:50]([O:57][NH2:58])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(OCC)(=O)C.[Pd].C(O)C.O1CCCC1>[CH2:50]([O:57][NH:58][C:8](=[O:7])[C@H:9]([N:20]([CH2:35][C:36]1[CH:41]=[CH:40][C:39]2[O:42][CH2:43][O:44][C:38]=2[CH:37]=1)[S:21]([C:24]1[C:29]([CH3:30])=[CH:28][C:27]([O:31][CH3:32])=[C:26]([CH3:33])[C:25]=1[CH3:34])(=[O:23])=[O:22])[C@@H:10]([OH:12])[CH3:11])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 102313O-BenzylhydroxylamineHCID 865900272(R)-[(3,4-methylenedioxybenzyl)-(4-methoxy-2,3,6-trimethylbenzene-sulfonyl)amino]-3(S)-(triethylsilyloxy)butyric acid 3,4-methylenedioxybenzyl ester

Product 1

HCID 18337567HCID 18337567, compoundYield 47.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of 2(R)-[(3,4-methylenedioxybenzyl)-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)amino]-3(S)-(triethylsilyloxy)butyric acid 3,4-methylenedioxybenzyl ester (3.3 g, 4.62 mmol) in argon deoxygenated 80% ethanol-tetrahydrofuran (100 mL) was added 10% Pd—C (2 g) and the resulting reaction mixture was hydrogenated at atmospheric pressure for 45 min. The reaction mixture was degassed under argon, the slurry was filtered over Celite, and the Celite pad was washed with ample 80% ethanol-methylene chloride. The filtrate was concentrated and azeotroped with tetrahydrofuran (200 mL) and the residue was dissolved in dimethylformamide (mL). O-Benzyl hydroxylamine (2.0 g,16.2 mmol), HOBT (0.71 g, 5.2 mmol), and EDAC (3.1 g, 16.2 mmol) were added and the reaction mixture was stirred for 16 h. The reaction mixture was diluted with ethyl acetate and was washed with 2.4 N aqueous hydrochloric acid and saturated aqueous sodium bicarbonate. The mixture was then dried over magnesium sulfate and concentrated in vacuo to afford crude N-benzyloxy-2(R)-[(3,4-methylenedioxy-benzyl)-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)amino]-3(S)-hydroxybutyramide (1.25 g) which was taken directly into the next reaction without further purification.

Workup

  1. customthe resulting reaction mixture
  2. customThe reaction mixture was degassed under argon
  3. filtrationthe slurry was filtered over Celite
  4. washthe Celite pad was washed with ample 80% ethanol-methylene chloride
  5. concentrationThe filtrate was concentrated
  6. customazeotroped with tetrahydrofuran (200 mL)
  7. dissolutionthe residue was dissolved in dimethylformamide (mL)
  8. washwas washed with 2.4 N aqueous hydrochloric acid and saturated aqueous sodium bicarbonate
  9. dry with materialThe mixture was then dried over magnesium sulfate
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9379244b0d074b05be47974586f8365f
Source dataset
uspto-grants-2002_12
Patent number
US06492394B1

Reaction notes

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