Triethylamine → HCID 58317738, compound

HRID 711526Notes

Reaction equation

HRID 711526 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-40ea0fc46b13498d89107477b7f22a39
Source dataset
uspto-grants-2015_11
Patent number
US09181255B2

Reaction notes

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