1,2-Dichloroethane → HCID 86679537, compound

HRID 1776584Notes

Reaction equation

HRID 1776584 reaction equation
[C:1]([O:5][C:6]([O:8][C:9]1[CH:21]=[CH:20][C:19]([N:22]([CH2:27][CH:28]2[CH2:30][CH2:29]2)[S:23]([CH3:26])(=[O:25])=[O:24])=[CH:18][C:10]=1[C:11]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:31][C:32]1[CH:33]=[N+:34]([O-:57])[CH:35]=[C:36]([Cl:56])[C:37]=1[CH2:38][C@@H:39]([C:41]1[CH:46]=[CH:45][C:44]([O:47][CH:48]([F:50])[F:49])=[C:43]([O:51][CH2:52][CH:53]2[CH2:55][CH2:54]2)[CH:42]=1)O.C(Cl)CCl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([O:5][C:6]([O:8][C:9]1[CH:21]=[CH:20][C:19]([N:22]([CH2:27][CH:28]2[CH2:29][CH2:30]2)[S:23]([CH3:26])(=[O:25])=[O:24])=[CH:18][C:10]=1[C:11]([O:13][CH2:14][C:15]([O:17][C@H:39]([C:41]1[CH:46]=[CH:45][C:44]([O:47][CH:48]([F:49])[F:50])=[C:43]([O:51][CH2:52][CH:53]2[CH2:54][CH2:55]2)[CH:42]=1)[CH2:38][C:37]1[C:36]([Cl:56])=[CH:35][N+:34]([O-:57])=[CH:33][C:32]=1[Cl:31])=[O:16])=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 71092687(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxideHCID 86679536HCID 86679536, compound

Product 1

HCID 86679537HCID 86679537, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-(2-(tert-butoxycarbonyloxy)-5-(N-(cyclopropylmethyl)-methylsulfonamido)benzoyloxy)acetic acid (0.215 g, 0.485 mmol), (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (204 g, 0.485 mmol), EDC (0.279 g, 1.454 mmol), and DMAP (0.059 g, 0.485 mmol) in DCM (25 mL) was stirred at RT overnight. The mixture was diluted with DCM and washed with 1N HCl and 5% NaHCO3. The organic phase was dried over sodium sulfate and the solvent was removed. The crude was purified by chromatography on silica gel cartridge (DCM:MeOH=99:1) affording (S)-4-(2-(2-(2-(tert-butoxycarbonyloxy)-5-(N-(cyclopropylmethyl)methylsulfonamido)-benzoyloxy)acetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (0.326 g, 0.385 mmol, 80% yield, MS/ESI+ 845.1 [MH]+).

Workup

  1. washwashed with 1N HCl and 5% NaHCO3
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customthe solvent was removed
  4. customThe crude was purified by chromatography on silica gel cartridge (DCM:MeOH=99:1)

Sources & evidence

ORD record
ord-1bd7f0f7d1b3421fa485e45ba0950626
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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