Diisopropylethylamine → HCID 86726824, compound

HRID 1499606Notes

Reaction equation

HRID 1499606 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:14]([OH:23])[C@@H:15]([CH:20]2[CH2:22][CH2:21]2)[CH2:16][N:17]=[N+]=[N-])(=O)=O)=CC=1.CCN(C(C)C)C(C)C>CO.[Pd]>[CH:20]1([C@H:15]2[CH2:16][NH:17][CH2:12][C@@H:13]([NH:24][C:25](=[O:26])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C@@H:14]2[OH:23])[CH2:22][CH2:21]1

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 86726823HCID 86726823, compound

Product 1

HCID 86726824HCID 86726824, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (2R,3R,4S)-5-azido-2-[(tert-butoxycarbonyl)amino]-4-cyclopropyl-3-hydroxypentyl 4-methylbenzenesulfonate (0.506 g, 1.11 mmol), DIPEA (0.31 mL, 1.8 mmol), and 10% palladium (dry basis) on activated carbon (wet, Degussa type E101 NE/W) (0.1 g) in MeOH (5 mL) was stirred under an atmosphere of hydrogen introduced via a balloon. After 3 h, the crude reaction mixture was filtered through a pad of diatomaceous earth and the solids were washed thoroughly with MeOH. The volatile organic solvents were removed under reduced pressure and the residue was dried under high vacuum to afford the sub-title compound as a solid. The crude product was used directly in the subsequent displacement reaction without further purification. LCMS (ESI) m/z calc. for C13H25N2O3 257.2 [M+H]+. found 257.2.

Workup

  1. additionintroduced via a balloon
  2. customthe crude reaction mixture
  3. filtrationwas filtered through a pad of diatomaceous earth
  4. washthe solids were washed thoroughly with MeOH
  5. customThe volatile organic solvents were removed under reduced pressure
  6. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-eb25d8e227fe4469a179ee7b1439ae46
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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