Methanesulfonyl chloride → HCID 86583562, compound

HRID 1066625Notes

Reaction equation

HRID 1066625 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH:15]([C:21]2[CH:26]=[C:25]([CH2:27][OH:28])[CH:24]=[C:23]([O:29][CH2:30][CH3:31])[CH:22]=2)[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][CH:9]=1)#[N:7].C(N(C(C)C)C(C)C)C>C1COCC1>[C:6]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH:15]([C:21]2[CH:26]=[C:25]([CH2:27][O:28][S:2]([CH3:1])(=[O:4])=[O:3])[CH:24]=[C:23]([O:29][CH2:30][CH3:31])[CH:22]=2)[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][CH:9]=1)#[N:7]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86583563HCID 86583563, compound

Product 1

HCID 86583562HCID 86583562, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methanesulphonyl chloride was added slowly at 0° C. to a solution of the ethyl (RS)-(4-cyano-phenylamino)-(3-ethoxy-5-hydroxymethyl-phenyl)-acetate (200 mg, 0.564 mmol) obtained in Example 234.2 and N-ethyldiisopropylamine (88 mg, 0.68 mmol) in THF (3 ml). The mixture was stirred for 1.5 h. at 0° C. and for 1.5 h. at room temperature. The mixture was poured into ice-water/1M HCl and extracted with EtOAc. The organic phase was washed with H2O, dried and filtered, and the filtrate was concentrated. There were obtained 232 mg of ethyl (RS)-(4-cyano-phenylamino)-(3-ethoxy-5-methanesulphonyloxymethyl-phenyl)-acetate as a yellow oil, which was used for the next reaction without additional purification.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with H2O
  3. customdried
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7fe564652d9143f58614ca9dbc94490a
Source dataset
uspto-grants-2001_06
Patent number
US06242644B1

Reaction notes

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