acetyl-DL-leucine → HCID 178474741, compound

HRID 1106115

Reaction equation

HRID 1106115 reaction equation
[C:1]([NH:4][CH:5]([C:10]([OH:12])=O)[CH2:6][CH:7]([CH3:9])[CH3:8])(=[O:3])[CH3:2].ClC(OCC(C)C)=O.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[N:33]=[C:32]([OH:34])[C:31]([C:35]([OH:37])=[O:36])=[CH:30][N:29]=2)=[CH:24][CH:23]=1>CN(C)C=O.C(N(CC)CC)C.ClCCl>[C:1]([NH:4][CH:5]([C:10]([NH:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]2[N:33]=[C:32]([OH:34])[C:31]([C:35]([OH:37])=[O:36])=[CH:30][N:29]=2)=[CH:26][CH:27]=1)=[O:12])[CH2:6][CH:7]([CH3:8])[CH3:9])(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 1995acetyl-DL-leucineHCID 62365Isobutyl chloroformateHCID 178507442HCID 178507442, compound

Product 1

HCID 178474741HCID 178474741, compoundYield 71.4%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent2×

Conditions

Temperature
-10 °C

Procedure

A solution of 13.0 g (75 mmol) of N-acetyl-DL-leucine, 10.5 ml (75 mmol) of triethylamine, and 150 ml of dichloromethane is stirred at -10° and 9.75 ml (75 mmol) of isobutyl chloroformate is added. The reaction mixture is stirred for 1/2 hour at -10° C. and a cold solution of 11.6 g (50 mmol) of 2-[4-aminophenyl)-4-hydroxy-5-pyrimidine carboxylic acid and 7.7 (55 mmol) of triethylamine in 200 ml of dimethylformamide is added. The mixture is stirred at 5° C. for 3 hrs and overnight at room temperature. The reaction mixture is evaporated and the residue treated with water. The pH is lowered to 2.5 with dilute hydrochloric acid and the solid filtered, washed with water, and dried to give 13.8 g of 2-[4-(N-acetyl-DL-leucylamino)phenyl]-4-hydroxy-5-pyrimidine carboxylic acid; mp 233°-235° C. dec.

Workup

  1. stirringThe mixture is stirred at 5° C. for 3 hrs and overnight at room temperature
  2. customThe reaction mixture is evaporated
  3. additionthe residue treated with water
  4. filtrationthe solid filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-fceb47acaddf4b658971068ab3942754
Source dataset
uspto-grants-1982_01
Patent number
US04311699

Linked notes

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