Water → HCID 118216479, compound

HRID 595257Notes

Reaction equation

HRID 595257 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.[OH:13][CH2:14][CH:15]1[C:19]2([CH2:21][CH2:20]2)[NH:18][C:17](=[O:22])[O:16]1.O>C(Cl)Cl>[CH3:1][S:2]([O:13][CH2:14][CH:15]1[C:19]2([CH2:21][CH2:20]2)[NH:18][C:17](=[O:22])[O:16]1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 91618405HCID 91618405, compound

Product 1

HCID 118216479HCID 118216479, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (1.36 g, 11.1 mmol) and triethylamine (2.51 mL, 18.4 mmol) were added to a solution of 7-(hydroxymethyl)-6-oxa-4-azaspiro[2.4]heptan-5-one (1.32 g, 9.2 mmol) in DCM (47 mL) at 0° C. and this mixture was stirred at room temperature for 3 hours. The reaction mixture was then poured into water and extracted with ethyl acetate (10 mL×3). The combined organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (ethyl acetate) to afford (5-oxo-6-oxa-4-azaspiro[2.4]hept-7-yl)methyl methanesulfonate. MS ESI calc'd. for C7H12NO5S [M+H]+ 222. found 222.

Workup

  1. extractionextracted with ethyl acetate (10 mL×3)
  2. dry with materialThe combined organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-19a6cdd7c1634542aaaf9414e2872b3a
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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