Methanesulfonyl chloride → HCID 12822511, compound

HRID 980294Notes

Reaction equation

HRID 980294 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]1([CH2:12][O:13][C:14](=[O:29])[NH:15][CH2:16][CH2:17][C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([CH2:27][NH2:28])[CH:25]=3)[NH:20][CH:19]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>N1C=CC=CC=1>[C:6]1([CH2:12][O:13][C:14](=[O:29])[NH:15][CH2:16][CH2:17][C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([CH2:27][NH:28][S:2]([CH3:1])(=[O:4])=[O:3])[CH:25]=3)[NH:20][CH:19]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 12803194HCID 12803194, compound

Product 1

HCID 12822511HCID 12822511, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulphonyl chloride (0.3 ml) was added in 3 portions over 3 h to a stirred, ice-cold solution of phenylmethyl[2-[5-(aminomethyl)-1H-indol-3-yl]ethyl]carbamate (0.45 g) in dry pyridine (15 ml). After a further 1 h, the mixture was partitioned between ice-cooled hydrochloric acid (1N, 300 ml) and ethyl acetate (200 ml). The organic layer was washed with brine (80 ml) and potassium carbonate solution (ca. 40%; 50 ml), dried (Na2SO4) and evaporated in vacuo to leave a yellow gum (0.45 g). Chromatography on silica gel (MFC: 18 g), eluting with increasing concentrations of ether in dichloromethane, gave the title compound (0.3 g) as an almost colourless oil.

Workup

  1. customthe mixture was partitioned between ice-
  2. temperaturecooled hydrochloric acid (1N, 300 ml) and ethyl acetate (200 ml)
  3. washThe organic layer was washed with brine (80 ml) and potassium carbonate solution (ca. 40%; 50 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-2e945abe32e64e88ab9d26ccbbbddd19
Source dataset
uspto-grants-1987_01
Patent number
US04636521

Reaction notes

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