(2S,3S)-2-Chloro-3-methylvaleric Acid → p-[5-(2,6-Dimethylheptyl)-pyrimidin-2-yl]-phenyl (S,S)-3-methyl-2-chloropentanoate

HRID 973711Notes

Reaction equation

HRID 973711 reaction equation
[CH3:1][C@@H:2]([CH2:8][CH3:9])[C@H:3]([Cl:7])[C:4]([OH:6])=[O:5].[CH3:10][CH:11]([CH2:26][CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:12][C:13]1[CH:14]=[N:15][C:16]([C:19]2[CH:24]=[CH:23][C:22](O)=[CH:21][CH:20]=2)=[N:17][CH:18]=1.C(OC(OCC)C(C[C@@H](C)CCCC(C)C)C(OCC)OCC)C>C(Cl)Cl>[CH3:1][C@@H:2]([CH2:8][CH3:9])[C@H:3]([Cl:7])[C:4]([O:6][C:22]1[CH:21]=[CH:20][C:19]([C:16]2[N:15]=[CH:14][C:13]([CH2:12][CH:11]([CH3:10])[CH2:26][CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])=[CH:18][N:17]=2)=[CH:24][CH:23]=1)=[O:5]

Participants

5

Reactant 3

HCID 11051847(2S,3S)-2-Chloro-3-methylvaleric AcidHCID 53766363(S)-1,1,3,3-tetraethoxy-2-(2,6-dimethylheptyl)-propaneHCID 136125432p-[5--(2,6-Dimethylheptyl)-pyrimidin-2-yl]phenol

Product 1

HCID 57237993p-[5-(2,6-Dimethylheptyl)-pyrimidin-2-yl]-phenyl (S,S)-3-methyl-2-chloropentanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 8 g of (S,S)-3-methyl-2-chloropentanoic acid, 16 g of optically active p-[5--(2,6-dimethylheptyl)-pyrimidin-2-yl]phenol [obtainable by condensation, known from the literature, of (S)-1,1,3,3-tetraethoxy-2-(2,6-dimethylheptyl)-propane with 4-hydroxyphenylamidine hydrochloride], 11.6 g of N,N-dicyclohexylcarbodiimide, 0.6 g of 4-N,N-dimethylaminopyridine and 300 ml of methylene chloride is stirred overnight at room temperature. After the urea derivative which has precipitated has been filtered off, the filtrate is washed with dilute hydrochloric acid and H2O and the organic phase is worked up in the customary manner. p-[5-(2,6-Dimethylheptyl)-pyrimidin-2-yl]-phenyl (S,S)-3-methyl-2-chloropentanoate is obtained.

Workup

  1. customobtainable by condensation
  2. customAfter the urea derivative which has precipitated
  3. filtrationhas been filtered off
  4. washthe filtrate is washed with dilute hydrochloric acid and H2O

Sources & evidence

ORD record
ord-5bcee076aaf44e0693936ec57a8aa534
Source dataset
uspto-grants-1991_11
Patent number
US05064569

Reaction notes

Loading…