Sarcosine t-butyl ester hydrochloride → HCID 86587112, compound

HRID 2084871Notes

Reaction equation

HRID 2084871 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.Cl.[C:23]([O:27][C:28](=[O:32])[CH2:29][NH:30][CH3:31])([CH3:26])([CH3:25])[CH3:24]>N1C=CC=CC=1.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([S:18]([N:30]([CH2:29][C:28]([O:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:32])[CH3:31])(=[O:20])=[O:19])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 11252350Sarcosine t-butyl ester hydrochlorideHCID 22645095HCID 22645095, compound

Product 1

HCID 86587112HCID 86587112, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

A solution of 0.57 g (1.67 mmol) of 4-[3-(4-chloro-phenyl)-prop-2-ynyloxy]-benzenesulfonyl chloride and 0.61 g (3.34 mmol, 2 eq) of sarcosine t-butyl ester hydrochloride in 0.51 mL of pyridine and 15 mL of chloroform was allowed to react overnight at room temperature. The reaction was concentrated in vacuo, diluted with water/ethyl acetate, neutralized with NaHCO3 and extracted with EtOAc (2×). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to afford a yellow oil which was purified via flash chormatography using 6:1 hexane:ethyl acetate to afford 0.396 g (53%) of tert-butyl [[(4-{[3-(4-chlorophenyl)-2-propynyl]oxy}phenyl)sulfonyl](methyl)amino]acetate as a white solid. Electrospray Mass Spec 450.4 (M+H)+.

Workup

  1. customto react overnight at room temperature
  2. concentrationThe reaction was concentrated in vacuo
  3. additiondiluted with water/ethyl acetate
  4. extractionextracted with EtOAc (2×)
  5. washThe combined organics were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford a yellow oil which
  10. customwas purified via flash chormatography

Sources & evidence

ORD record
ord-84cdc99b8b094ca7b6d97235ba12b5eb
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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