1,2-Dichloroethane → HCID 86679412, compound

HRID 1776456Notes

Reaction equation

HRID 1776456 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][CH2:36][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.O>[C:28]([O:32][C:33]([NH:35][CH2:36][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])([CH3:31])([CH3:30])[CH3:29]

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 78288N-(tert-butoxycarbonyl)glycineHCID 71092687HCID 71092687, compound

Product 1

HCID 86679412HCID 86679412, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (80 mg; 0.19 mmol) was dissolved in DMF (2 ml), then 2-(tert-butoxycarbonylamino)acetic acid (70 mg, 0.4 mmol), EDC (60 mg, 0.3 mmol), and DMAP (30 mg, 0.25 mmol) were added. The reaction was stirred at RT for 6 hours, then it was diluted with water and extracted with EtOAc. The organic phase was extracted with HCl 1M and with K2CO3 sat, dried over Na2SO4 and evaporated under vacuum to give 80 mg of the desired compound (Yield: 74%).

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic phase was extracted with HCl 1M and with K2CO3
  3. dry with materialdried over Na2SO4
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-06b47c10235e41b78e1e6933592af4f2
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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