Pyridine → HCID 66628460, compound

HRID 130511Notes

Reaction equation

HRID 130511 reaction equation
N1C=CC=CC=1.[Cl:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[Cl:17])[C:11](Cl)=[O:12].[CH2:18]([O:20][C:21]([C@:23]1([NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C@H:28]([NH2:29])[CH2:27][C@@H:26]2[C@H:24]1[C@@:25]2([F:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:22])[CH3:19]>C(Cl)(Cl)Cl>[CH2:18]([O:20][C:21]([C@:23]1([NH:36][C:37]([O:39][C:40]([CH3:42])([CH3:41])[CH3:43])=[O:38])[C@H:28]([NH:29][C:11](=[O:12])[C:10]2[CH:14]=[CH:15][C:16]([Cl:17])=[C:8]([Cl:7])[CH:9]=2)[CH2:27][C@@H:26]2[C@H:24]1[C@@:25]2([F:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:22])[CH3:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 66628652HCID 66628652, compound

Product 1

HCID 66628460HCID 66628460, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

7.3 μL of pyridine and 14 mg of 3,4-dichlorobenzoyl chloride were added to 17 mg of (1R,2R,3R,5R,6R)-3-amino-2-t-butoxycarbonylamino-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester dissolved in 0.17 mL of chloroform, and the mixture was stirred for 3 hours at room temperature. The reaction solution was concentrated under reduced pressure The residue was purified by column chromatography (silica gel: Wako gel C200 (made by Wako Pure Chemical Industries Ltd.), eluent: chloroform-ethanol=100:1), thereby yielding 21 mg of (1R,2R,3R,5R,6R)-2-t-butoxycarbonylamino-3-(3,4-dichlorobenzoylamino)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure The residue
  2. customwas purified by column chromatography (silica gel: Wako gel C200 (made by Wako Pure Chemical Industries Ltd.), eluent: chloroform-ethanol=100:1)

Sources & evidence

ORD record
ord-8a2d9f5b6b1d45e6ab5173eeb63c09b6
Source dataset
uspto-grants-2008_06
Patent number
US07381746B2

Reaction notes

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