Chloroform → HCID 86596753, compound

HRID 2053433Notes

Reaction equation

HRID 2053433 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13](Cl)=[O:14])=[C:5]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[NH2:22][C@H:23]([CH2:28][OH:29])[CH2:24][CH:25]([CH3:27])[CH3:26].C(Cl)(Cl)Cl>C(Cl)Cl>[OH:29][CH2:28][CH:23]([NH:22][C:13]([C:6]1[C:7](=[O:12])[NH:8][C:9]2[C:4]([C:5]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:3][C:2]([Cl:1])=[CH:11][CH:10]=2)=[O:14])[CH2:24][CH:25]([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 111307L-LeucinolHCID 87737979HCID 87737979, compound

Product 1

HCID 86596753HCID 86596753, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring suspension of 6-chloro-2-oxo-4-phenyl-1,2-dihydro-quinoline-3-carboxylic acid chloride (29 mg, 0.09 mmol) in DCM (0.5 mL) was added (S)-(+)-leucinol (30 μL, 0.23 mmol). Within 5 min, the mixture became homogeneous and the reaction was complete as determined by LCMS. Chloroform (2 mL) was added, and the solution was extracted with IN HCl (4×1 mL) and water (2×1 mL). The chloroform layer was purified directly by flash chromatography eluting with chloroform, then chloroform/methanol (100:1)->(50:1)->(25:1) to afford 6-chloro-2-oxo-4-phenyl-1,2-dihydro-quinoline-3-carboxylic acid (1-hydroxymethyl-3-methylbutyl)amide (b) (19 mg, 52%) as a white powder. MS: 399.2 (M+H).

Workup

  1. extractionthe solution was extracted with IN HCl (4×1 mL) and water (2×1 mL)
  2. customThe chloroform layer was purified directly by flash chromatography
  3. washeluting with chloroform

Sources & evidence

ORD record
ord-f116ee9a1620450cba9cf06d3c5b2e86
Source dataset
uspto-grants-2008_02
Patent number
US07326788B2

Reaction notes

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