Triethylamine → HCID 131735387, compound

HRID 630373Notes

Reaction equation

HRID 630373 reaction equation
C(N([CH2:6][CH3:7])CC)C.[O:8]=[C:9]([CH2:15][CH3:16])[CH2:10][CH2:11][C:12]([OH:14])=O.ClC([O:20][CH2:21][CH:22](C)C)=O.Cl.[OH:26][CH:27]1[O:35][C@H:34]([CH2:36][OH:37])[C@@H:32]([OH:33])[C@H:30]([OH:31])[C@@H:28]1[NH2:29].C([O:41][C:42](=O)[CH2:43]CC(=O)CC)(=O)O.[OH2:50].C1C[O:54][CH2:53][CH2:52]1>C1COCC1>[C:42]([O:26][CH:27]1[O:35][C@H:34]([CH2:36][O:37][C:6](=[O:50])[CH3:7])[C@@H:32]([O:33][C:21](=[O:20])[CH3:22])[C@H:30]([O:31][C:53](=[O:54])[CH3:52])[C@@H:28]1[NH:29][C:12](=[O:14])[CH2:11][CH2:10][C:9](=[O:8])[CH2:15][CH3:16])(=[O:41])[CH3:43]

Participants

8

Reactant 6

HCID 8471Triethylamine2×HCID 62365Isobutyl chloroformateHCID 37997744-Oxohexanoic acidHCID 9964480(3S,4R,5S,6R)-3-Amino-6-(hydroxymethyl)tetrahydro-2H-pyran-2,4,5-triol hydrochlorideHCID 21881883Oxolane--water (1/1)HCID 87511806HCID 87511806, compound

Product 1

HCID 131735387HCID 131735387, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.6 mL (19 mmol) of triethylamine in 56 mL of anhydrous THF was added 2.47 g (19 mmol) of 4-oxo-hexanoic acid (Sigma Aldrich, Milwaukee Wis.). The reaction was stirred for 15 min at rt under a N2 atmosphere after which 2.4 mL (19 mmol) of isobutyl chloroformate was added drop wise by a syringe. The reaction was stirred for 3.0 h during which time a white precipitate formed. The 4-oxo-hexanoic acid carbonic anhydride was used in the next step without further purification. To a solution of 3.6 g (17 mmol) of mannosamine hydrochloride in 112 mL of 1:1 H2O/THF was added 3.1 mL (22 mmol) of triethylamine. The solution was stirred for 15 min at rt after which the 4-oxo-hexanoic acid carbonic anhydride was added drop wise by an addition funnel. The reaction was stirred for another 36 h under a N2 atmosphere and the solution was concentrated in vacuo. The crude compound was acetylated by treatment with 40 mL of 2:1 Pyr/Ac2O. The reaction was stirred for 12 h at rt and then the solution was concentrated in vacuo. The resulting syrup was washed with 1.0 M HCl (2×30 mL) and saturated NaHCO3 (1×30 mL), then dried over Na2SO4. Purification of the crude compound by silica gel chromatography yielded a white foam.

Workup

  1. additionwas added drop wise by a syringe
  2. customformed
  3. customThe 4-oxo-hexanoic acid carbonic anhydride was used in the next step without further purification
  4. additionwas added drop wise by an addition funnel
  5. stirringThe reaction was stirred for another 36 h under a N2 atmosphere
  6. concentrationthe solution was concentrated in vacuo
  7. stirringThe reaction was stirred for 12 h at rt
  8. concentrationthe solution was concentrated in vacuo
  9. washThe resulting syrup was washed with 1.0 M HCl (2×30 mL) and saturated NaHCO3 (1×30 mL)
  10. dry with materialdried over Na2SO4
  11. customPurification of the crude compound by silica gel chromatography
  12. customyielded a white foam

Sources & evidence

ORD record
ord-30d71f68d27d4b11b9b7e158226b62ce
Source dataset
uspto-grants-2016_04
Patent number
US09315532B2

Reaction notes

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