2-Chloroethyl methyl ether → (RS,SR)-2-benzenesulfonyl-2-(6-chloro-9-methoxymethyl-2,3,4,9-tetrahydro-1H-carbazol-2yl)-propionic acid methyl ester

HRID 602755Notes

Reaction equation

HRID 602755 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C:4]([S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:22])=[O:21])([CH:6]1[CH2:18][CH2:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([Cl:19])[CH:14]=3)[NH:9][C:8]=2[CH2:7]1)[CH3:5].[H-].[Na+].ClC[CH2:34][O:35][CH3:36]>C1COCC1>[CH3:1][O:2][C:3](=[O:29])[C:4]([S:20]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)(=[O:22])=[O:21])([CH:6]1[CH2:18][CH2:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([Cl:19])[CH:14]=3)[N:9]([CH2:34][O:35][CH3:36])[C:8]=2[CH2:7]1)[CH3:5]

Participants

5

Reactant 3

HCID 123162-Chloroethyl methyl etherHCID 24758Sodium hydrideHCID 11419051HCID 11419051, compound

Product 1

HCID 67267086(RS,SR)-2-benzenesulfonyl-2-(6-chloro-9-methoxymethyl-2,3,4,9-tetrahydro-1H-carbazol-2yl)-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

350 mg (0.81 mmol) of (RS,SR)-2-benzenesulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propionic acid methyl ester (from example 3) in 10 mL of THF at 0° C., were treated with 39 mg (0.89 mmol, 1.1 eq) of NaH (55% in oil) portionwise within 30 min. 0.10 mL (1.22 mmol, 1.5 eq) of 1-chloro-2-methoxy-ethane was added and the ice bath removed. After 2 hours, the reaction was quenched by addition of aqueous NH4Cl sat., extracted with EtOAc and the organic phases dried over Na2SO4. Evaporation of the solvent afforded (RS,SR)-2-benzenesulfonyl-2-(6-chloro-9-methoxymethyl-2,3,4,9-tetrahydro-1H-carbazol-2yl)-propionic acid methyl ester as yellow solid, MS: 493 (MNH4′). The crude material was used in the next step without further purification.

Workup

  1. customthe ice bath removed
  2. customthe reaction was quenched by addition of aqueous NH4Cl sat.
  3. extractionextracted with EtOAc
  4. dry with materialthe organic phases dried over Na2SO4
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-41f47a1717b8438d9816bfbcadf2a372
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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