Triethylamine → (R)-2-(((Benzyloxy)carbonyl)amino)pentane-1,5-diyl dimethanesulfonate

HRID 7287Notes

Reaction equation

HRID 7287 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C@@H:5]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][OH:7].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:26][S:27]([O:7][CH2:6][C@H:5]([NH:8][C:9]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:18])[CH2:4][CH2:3][CH2:2][O:1][S:27]([CH3:26])(=[O:29])=[O:28])(=[O:29])=[O:28]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 2757382(R)-Benzyl (1,5-dihydroxypentan-2-yl)carbamate

Product 1

HCID 66524788(R)-2-(((Benzyloxy)carbonyl)amino)pentane-1,5-diyl dimethanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of benzyl (1R)-4-hydroxy-1-(hydroxymethyl)butylcarbamate (1.5 g) in DCM (60 ml) was treated with triethylamine (3.3 ml) and stirred at room temperature for 10 min. Methanesulphonyl chloride (1.34 ml) was then added dropwise and the resultant mixture stirred at 0° C. for 75 min. Sodium bicarbonate solution was added and the reaction mixture allowed to reach room temperature over 1 h. The organic layer was separated, washed with brine, dried (over magnesium sulphate) and concentrated under reduced pressure to give a yellow oil. The oil was purified using Biotage™ chromatography (eluting with hexane:ethyl acetate 1:2, 1:3) to give the title compound (1.924 g) as a yellow oil

Workup

  1. waitto reach room temperature over 1 h
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (over magnesium sulphate)
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow oil
  7. customThe oil was purified
  8. washBiotage™ chromatography (eluting with hexane:ethyl acetate 1:2, 1:3)

Sources & evidence

ORD record
ord-f0d992a9a8f14e6b9e4f8b4467f7e8d6
Source dataset
uspto-grants-2006_08
Patent number
US07084139B2

Reaction notes

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