1,2-Dichloroethane → HCID 86679573, compound

HRID 1776612Notes

Reaction equation

HRID 1776612 reaction equation
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:27])[CH:5]=[C:6]([Cl:26])[C:7]=1[CH2:8][C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[C:13]([O:21][CH2:22][CH:23]2[CH2:25][CH2:24]2)[CH:12]=1)[OH:10].[C:28]([O:32][C:33]([NH:35][C@@H:36]([CH2:40][C:41]1[CH:46]=[CH:45][C:44]([O:47][S:48]([CH3:51])(=[O:50])=[O:49])=[CH:43][CH:42]=1)[C:37](O)=[O:38])=[O:34])([CH3:31])([CH3:30])[CH3:29].C(Cl)CCl>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:28]([O:32][C:33]([NH:35][C@@H:36]([CH2:40][C:41]1[CH:42]=[CH:43][C:44]([O:47][S:48]([CH3:51])(=[O:50])=[O:49])=[CH:45][CH:46]=1)[C:37]([O:10][C@H:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[C:13]([O:21][CH2:22][CH:23]2[CH2:25][CH2:24]2)[CH:12]=1)[CH2:8][C:7]1[C:6]([Cl:26])=[CH:5][N+:4]([O-:27])=[CH:3][C:2]=1[Cl:1])=[O:38])=[O:34])([CH3:30])([CH3:31])[CH3:29]

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 86679572HCID 86679572, compound

Product 1

HCID 86679573HCID 86679573, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (100 mg, 0.24 mmol) and (S)-2-(tert-butoxycarbonyl-amino)-3-(4-(methylsulfonyloxy)phenyl)propanoic acid (172 mg, 0.48 mmol) were dissolved in DMF (3 ml). DMAP (35 mg, 0.29 mmol) and EDC (92 mg, 0.48 mmol) were added, and the mixture was stirred at RT for 3 hours, then was quenched with HCl 1N and extracted with EtOAc. The organic layer was washed with HCl 1N and NaHCO3 sat. sol., then was dried over Na2SO4 and evaporated under vacuum to give 155 mg (85%) of the title compound which was employed in the next step without any further purification. MS/ESI+ 761.14 [MH]+.

Workup

  1. customwas quenched with HCl 1N
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with HCl 1N and NaHCO3 sat. sol.
  4. dry with materialwas dried over Na2SO4
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-f308748768dd4a7daf0144e0c8846ae9
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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