Water → HCID 59619202, compound

HRID 1367552Notes

Reaction equation

HRID 1367552 reaction equation
[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[Cl:24])(=[O:16])=[O:15])[CH2:11][C@H:10]2[CH2:25][O:26]CC2C=CC(OC)=CC=2)=[O:8])[CH2:5][CH2:4]1)#[N:2].O>ClCCl>[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[Cl:24])(=[O:15])=[O:16])[CH2:11][C@H:10]2[CH2:25][OH:26])=[O:8])[CH2:5][CH2:4]1)#[N:2]

Participants

4

Reactant 2

HCID 962WaterHCID 59619362HCID 59619362, compound

Product 1

HCID 59619202HCID 59619202, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold mixture of (1R,2R,4S)-4-(2-Chloro-4-fluoro-benzenesulfonyl)-2-(4-methoxy-benzyloxymethyl)-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide (example 153, step 9, 171 mg) in dichloromethane (4 mL) was added water (0.2 mL) and dichlorodicyanoquinone (97 mg). The reaction mixture was stirred 90 min at room temperature. The suspension was filtered and the solid was washed with dichloromethane. The resulting liquor was partionned between dichloromethane and saturated aqueous solution of sodium hydrogenocarbonate. The aqueous layer was washed with dichloromethane. The combined organic layers were washed brine, dried over sodium sulfate, filtered and evaporated in vacuo. The residue was purified by flash chromatography on silica gel with a gradient of dichlormethane:methanol (98:2 to 19:1 v/v) as eluant to afford the title compound (101 mg, 77%) as a white solid. MS (EI): 401.1 (M+H)+.

Workup

  1. filtrationThe suspension was filtered
  2. washthe solid was washed with dichloromethane
  3. washThe aqueous layer was washed with dichloromethane
  4. washThe combined organic layers were washed brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel with a gradient of dichlormethane:methanol (98:2 to 19:1 v/v) as eluant

Sources & evidence

ORD record
ord-1b258d13f53a49a79c6550722476dabb
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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