Aniline → HCID 20482846, compound

HRID 1389368Notes

Reaction equation

HRID 1389368 reaction equation
Br[CH:2]([CH:8]([OH:10])[CH3:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].CN(P(N(C)C)(N(C)C)=O)C.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CCOCC>[C:23]1([NH:22][CH:2]([CH:8]([OH:10])[CH3:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 12679HexamethylphosphoramideHCID 12541051Ethyl 2-bromo-3-hydroxybutanoate

Product 1

HCID 20482846HCID 20482846, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of ethyl 2-bromo-3-hydroxybutanoate (10 g) and 15 ml of HMPT is added 13.2 g of aniline. The reaction is stirred at RT for 3 days and then taken up in ether followed by washing with dilute sulfuric acid, pH 3, and water. The ether phase is dried over magnesium sulfate and evaporated to yield ethyl 2-phenylamino-3-hydroxybutanoate, which is saponified using 1.6 g of sodium hydroxide, 40 ml of methanol and 20 ml of water with stirring overnight at RT. The acid 2-phenylamino-3-hydroxybutanoic acid (3.0 g) is reacted with m-phenoxybenzyl bromide (3.4 g) in HMPT (20 ml) and potassium carbonate (2.12 g) at 35° for a few hours and worked up using ether/water to yield the m-phenoxybenzyl ester of 2-phenylamino-3-hydroxybutanoic acid.

Workup

  1. washby washing with dilute sulfuric acid, pH 3, and water
  2. dry with materialThe ether phase is dried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-035f93c2cc0f44ca80e6432b7212fc88
Source dataset
uspto-grants-1981_01
Patent number
US04243819

Reaction notes

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