Methanesulfonyl chloride → HCID 86583562, compound

HRID 1016791Notes

Reaction equation

HRID 1016791 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-e2b5c0a9d93e4948b6be0a0aba99175b
Source dataset
uspto-grants-2002_11
Patent number
US06476264B2

Reaction notes

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