Triethylamine → HCID 59363822, compound

HRID 1430638Notes

Reaction equation

HRID 1430638 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[S:9][CH:10]=[C:11]([CH2:13][CH2:14][OH:15])[N:12]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:7][C:8]1[S:9][CH:10]=[C:11]([CH2:13][CH2:14][O:15][S:25]([CH3:24])(=[O:27])=[O:26])[N:12]=1)=[O:16])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22405510tert-Butyl (4-(2-hydroxyethyl)thiazol-2-yl)carbamate

Product 1

HCID 59363822HCID 59363822, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-(2-Hydroxy-ethyl)-thiazol-2-yl]-carbamic acid tert-butyl ester (5 g, 20 mmol) and triethyl amine (5.8 ml, 40 mmol) in DCM (50 ml) was added methanesulfonyl chloride (1.9 ml, 24 mmol) slowly over a period of 10-15 min. The reaction mixture was stirred at r.t. for 4 hr, quenched with brine (10 ml) and extracted in DCM (100 ml), dried over Na2SO4 and passed through a short column of silica gel bed and concentrated to obtain methanesulfonic acid 2-(2-tert-butoxycarbonylamino-thiazol-4-yl)-ethyl ester (6.0 g, 90%) which was used as such for the next step without further purification.

Workup

  1. customquenched with brine (10 ml)
  2. extractionextracted in DCM (100 ml)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bf168c3852564773a741ae91043e91fc
Source dataset
uspto-grants-2015_01
Patent number
US08940900B2

Reaction notes

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