Triethylamine → HCID 86652495, compound

HRID 2205192Notes

Reaction equation

HRID 2205192 reaction equation
[P:1](Cl)(Cl)(=[O:9])[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl-:12].[CH2:13]([O:20][C:21](=[O:25])[C@@H:22]([NH3+:24])[CH3:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>ClCCl>[Cl:12][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][P:1](=[N:24][C@@H:22]([CH3:23])[C:21]([O:20][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:25])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13038Phosphorodichloridic acid, phenyl esterHCID 178462210HCID 178462210, compound

Product 1

HCID 86652495HCID 86652495, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phenyl phosphorodichloridate (1.17 g, 2 N) was added to a solution of 43 (1 g, 5.58 mmol) in dichloromethane at −78° C. Triethylamine (1.13 g, 11.173 mmol) was then added drop-wise. Once complete, the reaction mixture was allowed to warm to room temperature and then evaporated to dryness under reduced pressure. Purification by silica gel chromatography [petroleum ether:ethyl acetate (3:1)] provided 44 as an colorless oil (1.2 g, 60%). LC-MS (M+H)+=354

Workup

  1. customevaporated to dryness under reduced pressure
  2. customPurification by silica gel chromatography [petroleum ether:ethyl acetate (3:1)]

Sources & evidence

ORD record
ord-58dc8d688bb64924b8c894b40e790f96
Source dataset
uspto-grants-2016_06
Patent number
US09370569B2

Reaction notes

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