4-Methoxybenzenesulfonyl chloride → HCID 6977080, compound

HRID 2393100Notes

Reaction equation

HRID 2393100 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:17])[C@@H:5]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[NH2:6].CN1CCOCC1.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>C(Cl)Cl.C(OCC)(=O)C>[CH3:2][O:3][C:4](=[O:17])[C@H:5]([NH:6][S:33]([C:30]1[CH:29]=[CH:28][C:27]([O:26][CH3:25])=[CH:32][CH:31]=1)(=[O:35])=[O:34])[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1

Participants

6

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 79724-MethylmorpholineHCID 11448200methyl (2R)-2-amino-3-(1H-indol-3-yl)propanoate hydrochloride

Product 1

HCID 6977080HCID 6977080, compoundYield 67.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of D-tryptophan methyl ester hydrochloride (4 mmol) in 40 mL of methylene chloride, magnetically stirred and cooled in an ice bath, under a nitrogen atmosphere, is added 8 mmol of NMM and 4 mmol of 4-methoxybenzene sulfonyl chloride. The mixture is allowed to come to ambient temperature overnight. It is diluted with ethyl acetate and washed twice with aqueous 10% HCl, then successively with water, 1M sodium bicarbonate, and brine. The organic solution is dried over sodium sulfate and concentrated to afford 1.05 g (65%) of a white solid, m.p. 120°-122° C.

Workup

  1. temperaturecooled in an ice bath, under a nitrogen atmosphere
  2. washwashed twice with aqueous 10% HCl
  3. dry with materialThe organic solution is dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-52dddf5664cc4979b1cab547cbb48bc1
Source dataset
uspto-grants-1998_09
Patent number
US05804593

Reaction notes

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