Triethylamine → HCID 86644158, compound

HRID 1523643Notes

Reaction equation

HRID 1523643 reaction equation
[OH:1][N:2]=[C:3]([Cl:17])[C@H:4]1[C@H:8]([CH2:9][O:10][CH3:11])[O:7][C:6]2([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[O:5]1.[CH3:18][S:19](Cl)(=[O:21])=[O:20].C(N(CC)CC)C>CCOCC>[CH3:11][O:10][CH2:9][C@@H:8]1[O:7][C:6]2([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[O:5][C@H:4]1[C:3]([Cl:17])=[N:2][O:1][S:19]([CH3:18])(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86644157HCID 86644157, compound

Product 1

HCID 86644158HCID 86644158, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(2R,3S)—N-hydroxy-3-(methoxymethyl)-1,4-dioxaspiro[4.5]decane-2-carbimidoyl chloride (35.6 g, 135.0 mmol) was dissolved in Et2O (600 mL) and cooled in an ice bath. Methanesulfonyl chloride (10.49 ml, 135.0 mmol) was added, followed by dropwise addition of triethylamine (18.82 ml, 135.0 mmol). The reaction was stirred for 30 minutes and then filtered and concentrated. The residue was purified on 1 Kg SiO2 (1 to 5% EtOAc in CH2Cl2) to afford (2R,3S)-3-(methoxymethyl)-N-(methylsulfonyloxy)-1,4-dioxaspiro[4.5]decane-2-carbimidoyl chloride (22.6 g, 66.12 mmol, 48.98% yield).

Workup

  1. temperaturecooled in an ice bath
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was purified on 1 Kg SiO2 (1 to 5% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-bf50160ca2c54689939d9d06ffac6fd5
Source dataset
uspto-grants-2015_07
Patent number
US09079890B2

Reaction notes

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