Aniline → HCID 20482846, compound

HRID 648272Notes

Reaction equation

HRID 648272 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 hydoxide, 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-fbb38a915a2d4809b58f56c5840d665f
Source dataset
uspto-grants-1983_10
Patent number
US04411912

Reaction notes

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