Ethyl ketone → HCID 11711011, compound

HRID 131655Notes

Reaction equation

HRID 131655 reaction equation
Cl.[OH:2][C:3]([CH3:23])([CH3:22])[CH2:4][CH2:5][CH2:6][CH:7]([C:9]1[S:13][C:12]([NH:14][C:15](=[O:21])[C@@H:16]([NH2:20])[CH2:17][CH2:18][CH3:19])=[N:11][CH:10]=1)[CH3:8].[CH3:24][CH2:25][C:26](=O)[CH2:27][CH3:28].C([O-])(=O)C.[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+].C([BH3-])#N.[Na+]>C(O)(=O)C.ClC(Cl)C>[OH:2][C:3]([CH3:22])([CH3:23])[CH2:4][CH2:5][CH2:6][CH:7]([C:9]1[S:13][C:12]([NH:14][C:15](=[O:21])[C@@H:16]([NH:20][CH:26]([CH2:27][CH3:28])[CH2:25][CH3:24])[CH2:17][CH2:18][CH3:19])=[N:11][CH:10]=1)[CH3:8]

Participants

8

Reactant 5

HCID 7288Ethyl ketoneHCID 24436Sodium SulfateHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 131726919HCID 131726919, compound

Product 1

HCID 11711011HCID 11711011, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 2-(S)-amino-pentanoic acid [5-(5-hydroxy-1,5-dimethyl-hexyl)-thiazol-2-yl]-amide HCl salt (200 mg, 0.55 mmol) and 3-pentanone (237 mg, 2.76 mmol), 5 drops of acetic acid, sodium acetate (100 mg), sodium sulfate (100 mg) and sodium cyanoborohydride (222 mg, 2.75 mmol) in dichloroethane (15 mL) was stirred at 40° C. overnight. The mixture was quenched with water, and extracted with methylene chloride. The organic layer was concentrated to dryness. The residue was purified by Shimadzu HPLC to give 2-(S)-(1-ethyl-propylamino)-pentanoic acid [5-(5-hydroxy-1,5-dimethyl-hexyl)-thiazol-2-yl]-amide as a colorless oil, LC-MS, RT=1.6 min, M+1=398.6.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with methylene chloride
  3. concentrationThe organic layer was concentrated to dryness
  4. customThe residue was purified by Shimadzu HPLC

Sources & evidence

ORD record
ord-971115c9267b4867911291f4b78ba108
Source dataset
uspto-grants-2008_06
Patent number
US07384968B2

Reaction notes

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