Sulfuric Acid → N-phenylvaline

HRID 1389337Notes

Reaction equation

HRID 1389337 reaction equation
Br[CH:2]([CH:22]([CH3:24])[CH3:23])[C:3]([O:5]C(C#N)C1C=CC=C(OC2C=CC=CC=2)C=1)=[O:4].[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[I-].[K+].S(=O)(=O)(O)O>CN(P(N(C)C)(N(C)C)=O)C>[C:26]1([NH:25][C@H:2]([C:3]([OH:5])=[O:4])[CH:22]([CH3:24])[CH3:23])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 4875Potassium IodideHCID 6115AnilineHCID 13705788alpha-Cyano-m-phenoxybenzyl alpha-bromoisovalerate

Product 1

HCID 10867191N-phenylvaline

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

To m-phenoxy-α-cyanobenzyl α-bromoisovalerate (2.0 g, 0.0052 mole) in 4 ml of HMPT, at 24°, is added aniline (1.5 g, 0.016 mole) and potassium iodide (21 mg). The reaction is stirred at 65° for 90 hours and then cooled and poured into ice-water (20 ml) plus 2 N sulfuric acid (10 ml). The reaction is worked up as in Example 4 and purified by preparative TLC to give the m-phenoxy-α-cyanobenzyl ester of N-phenylvaline.

Workup

  1. temperaturecooled
  2. custompurified by preparative TLC

Sources & evidence

ORD record
ord-530b84e2c4544fc5b193c39cc41ecdf5
Source dataset
uspto-grants-1981_01
Patent number
US04243819

Reaction notes

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