Triethylamine → HCID 10004506, compound

HRID 898559Notes

Reaction equation

HRID 898559 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:10]=[C:11]([NH:19][C:20](=[O:31])[CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=2[Cl:30])[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][CH:17]=O.Cl.[NH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.C1COCC1>[Cl:8][C:9]1[CH:10]=[C:11]([NH:19][C:20](=[O:31])[CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=2[Cl:30])[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][CH2:17][NH:33][CH2:34][C:35]([O:37][CH3:38])=[O:36]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 122755Glycine methyl ester hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 59691596HCID 59691596, compound

Product 1

HCID 10004506HCID 10004506, compound

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

75 μL (0.54 mmol) of triethylamine and 70 mg (0.18 mmol) of N-[3-chloro-4-(2-oxo -ethoxy)-phenyl]-2-(2,4-dichloro-phenoxy)-acetamide was added to a suspension of 45 mg (0.36 mmol) of methyl amino-acetate hydrochloride in 2 mL dichloromethane/THF (1:1). 114 mg (0.54 mmol) of sodium triacetoxyborohydride was added and the mixture was stirred for 3 hours at RT. 100 mL of 2 N aqueous sodium carbonate solution was added and the aqueous phase was exhaustively extracted with chloroform. The combined org. extracts were dried over magnesium sulphate, evaporated down i. vac. and purified by column chromatography (silica gel, EtOAc/MeOH 9:1).

Workup

  1. extractionthe aqueous phase was exhaustively extracted with chloroform
  2. dry with materialextracts were dried over magnesium sulphate
  3. customevaporated down i
  4. customand purified by column chromatography (silica gel, EtOAc/MeOH 9:1)

Sources & evidence

ORD record
ord-332602f3a75144a9bf934fc6a3e2cddf
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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