Triethylamine → HCID 58317738, compound

HRID 2092830Notes

Reaction equation

HRID 2092830 reaction equation
CCN(CC)CC.[N:8]([C@H:11]1[CH2:15][C@@H:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][C@@H:12]1[OH:24])=[N+:9]=[N-:10].[CH3:25][S:26](Cl)(=[O:28])=[O:27].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:25][S:26]([O:24][C@@H:12]1[CH2:13][C@H:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:15][C@H:11]1[N:8]=[N+:9]=[N-:10])(=[O:28])=[O:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 11128207HCID 11128207, compound

Product 1

HCID 58317738HCID 58317738, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled mixture of Et3N (9.49 g, 94.0 mmol) and (1S,2S,4R)-2-azido-4-(benzyloxy)cyclopentanol (18.25 g, 78.3 mmol) in DCM (500 mL) was added dropwise methanesulfonyl chloride (9.87 g, 86.2 mmol) in DCM (50 mL) at 0° C. The mixture was stirred overnight at a temperature of 0° C. to RT. After complete conversion, aq NaHCO3 (5%, 300 mL) was added. The mixture was extracted with DCM, washed with brine, and dried over Na2SO4 to give the title compound as an oil (23.58 g, 75.8 mmol). 1H NMR (400 MHz, CDCl3) δ ppm 1.83-1.89 (m, 1H), 2.06-2.13 (m, 1H), 2.34-2.49 (m, 2H), 3.04 (s, 3H), 3.94-3.99 (m, 1H), 4.08-4.13 (m, 1H), 4.64 (s, 2H), 4.93-4.98 (q, J=5.6/7.0 Hz, 1H), 7.25-7.36 (m, 5H).

Workup

  1. extractionThe mixture was extracted with DCM
  2. washwashed with brine
  3. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-6f3f5f609e704bdea0f7a971a3e0ece2
Source dataset
uspto-grants-2013_05
Patent number
US08440689B2

Reaction notes

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