Water → N,N'-di-Boc-2-methanesulfonyloxy-1,3-diaminopropane

HRID 879967Notes

Reaction equation

HRID 879967 reaction equation
[C:1]([NH:8][CH2:9][CH:10]([OH:20])[CH2:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].O>C(Cl)Cl>[C:13]([NH:12][CH2:11][CH:10]([O:20][S:29]([CH3:28])(=[O:31])=[O:30])[CH2:9][NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 375632tert-butyl N-{3-[(tert-butoxycarbonyl)amino]-2-hydroxypropyl}carbamate

Product 1

HCID 14839452N,N'-di-Boc-2-methanesulfonyloxy-1,3-diaminopropaneYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N,N′-di-Boc-2-hydroxy-1,3-diaminopropane (13.19 g, 45.4 mmol) and triethylamine (1.5 eq, 9.5 ml, 68.1 mmol) in dry 50 ml CH2Cl2 was added dropwise a solution of methanesulfonyl chloride (1.5 eq, 5.25 ml, 68 mmol) in dry 15 ml CH2Cl2 over a period of 1 h at 0° C. with stirring under nitrogen. After the addition, the reaction was stirred overnight at room temperature. Water was slowly added to quench the reaction; the organic layer was separated and then washed with water (5×15 ml) and dried over Na2SO4 and evaporated to give white solid. Recrystallization from hot acetone and cyclohexane gave 10.36 g (62%) white solid. M.p.=127° C.

Workup

  1. additionAfter the addition
  2. stirringthe reaction was stirred overnight at room temperature
  3. customto quench
  4. customthe reaction
  5. customthe organic layer was separated
  6. washwashed with water (5×15 ml)
  7. dry with materialdried over Na2SO4
  8. customevaporated
  9. customto give white solid
  10. customRecrystallization from hot acetone and cyclohexane

Sources & evidence

ORD record
ord-0eeceb69d2864ba39f2631a21a1a6e59
Source dataset
uspto-grants-2015_03
Patent number
US08993544B2

Reaction notes

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