Ethyl Acetate → HCID 86653235, compound

HRID 510647Notes

Reaction equation

HRID 510647 reaction equation
[OH:1][CH2:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].C(OCC)(=O)C>O1CCCC1.[Cl-].[Na+].O>[CH3:28][S:29]([O:1][CH2:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][CH2:8][NH:9][C:10]([O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:16])=[CH:5][CH:4]=1)(=[O:31])=[O:30]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 22337080tert-Butyl 4-(hydroxymethyl)phenethylcarbamate

Product 1

HCID 86653235HCID 86653235, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of tert-butyl 4-(hydroxymethyl)phenethylcarbamate (2.51 g, 9.99 mmol) and N,N-diisopropylethylamine (1.9 mL, 11 mmol) in tetrahydrofuran (50 mL) was stirred and cooled in an ice bath. Methanesulfonyl chloride (0.85 mL, 11 mmol) was added in several portions, and stirring was continued in the bath for 50 minutes. The reaction mixture was transferred to a separatory funnel containing ethyl acetate (200 mL) and brine (200 mL). The organic layer was dried over sodium sulfate and concentrated to afford 4-(2-(tert-butoxycarbonylamino)ethyl)benzyl methanesulfonate as a soft white solid. (3.29 g, 100% yield).

Workup

  1. temperaturecooled in an ice bath
  2. customThe reaction mixture was transferred to a separatory funnel
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6a926f24affb4f7db7a04add729cecee
Source dataset
uspto-grants-2015_08
Patent number
US09096567B2

Reaction notes

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