Methanesulfonyl chloride → HCID 86679506, compound

HRID 1776550Notes

Reaction equation

HRID 1776550 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:12][CH2:11]1.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>N1C=CC=CC=1>[CH:10]1([CH2:9][O:8][C:7]2[CH:6]=[CH:5][C:4]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:3][C:2]=2[NH:1][S:19]([CH3:18])(=[O:21])=[O:20])[CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86679505HCID 86679505, compound

Product 1

HCID 86679506HCID 86679506, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of crude methyl 2-(3-amino-4-(cyclopropylmethoxy)phenyl)acetate (theoric 4.74 mmol) in pyridine (50 ml), methanesulfonyl chloride (0.406 ml, 5.10 mmol) was added, and the mixture was reacted for 3 hours at RT. The solvent was evaporated to dryness, and the residue was partitioned between EtOAc and HCl 1N; the aqueous phase was extracted with EtOAc (3×), and the combined organic layers were dried over Na2SO4. The solvent was removed under vacuum affording methyl 2-(4-(cyclopropylmethoxy)-3-(methylsulfonamido)phenyl)acetate (1.4 g, 4.47 mmol, 94.3% yield over 3 steps, MS/ESI+ 313.9 [MH]+). This intermediate was used without any additional purification.

Workup

  1. customthe mixture was reacted for 3 hours at RT
  2. customThe solvent was evaporated to dryness
  3. customthe residue was partitioned between EtOAc and HCl 1N
  4. extractionthe aqueous phase was extracted with EtOAc (3×)
  5. dry with materialthe combined organic layers were dried over Na2SO4
  6. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-7fe779a2b8034b58944afd394afc7dd8
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

Loading…