Triethylamine → HCID 86659127, compound

HRID 1260395Notes

Reaction equation

HRID 1260395 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][C:7]([O:10][C:11]([NH:13][C@@H:14]1[C@@H:19]([OH:20])[CH2:18][CH2:17][O:16][CH2:15]1)=[O:12])([CH3:9])[CH3:8].C(N(CC)CC)C>C(Cl)Cl>[CH3:9][C:7]([O:10][C:11]([NH:13][C@@H:14]1[C@@H:19]([O:20][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:18][CH2:17][O:16][CH2:15]1)=[O:12])([CH3:6])[CH3:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 669895551,5-Anhydro-2,4-dideoxy-2-[[(1,1-dimethylethoxy)carbonyl]amino]-L-threo-pentitol

Product 1

HCID 86659127HCID 86659127, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

Methanesulfonyl chloride (30 ml) in DCM (100 ml) was added dropwise to a solution of 1,5-an hydro-2,4-dideoxy-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-L-threo-pentitol (75 g) and triethylamine (58 ml) in DCM (900 ml) at 0° C., maintaining the temperature below 3° C. during the addition. The mixture was stirred for 30 min, warmed to 25° C. and stirred for 2 h. The reaction mixture was washed with water (2×1.4 l), the organic phase dried and the solvent evaporated to give 1,5-anhydro-2,4-dideoxy-2-({[(1,1-dimethylethy)oxy]carbonyl}amino)-3-O-(methylsulfonyl)-L-threo-pentitol (103.1 g).

Workup

  1. temperaturemaintaining the temperature below 3° C.
  2. additionduring the addition
  3. stirringstirred for 2 h
  4. washThe reaction mixture was washed with water (2×1.4 l)
  5. customthe organic phase dried
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-80aa212dd8904463bd4c80af9f5b7678
Source dataset
uspto-grants-2013_06
Patent number
US08470835B2

Reaction notes

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