Acetic Acid → HCID 85432458, compound

HRID 1767024Notes

Reaction equation

HRID 1767024 reaction equation
[CH3:1][CH2:2][C:3](=O)[CH2:4][CH3:5].[CH3:7][C:8]([C:13]1[S:17][C:16]([NH:18][C:19](=[O:25])[CH:20]([NH2:24])[CH2:21][CH2:22][CH3:23])=[N:15][N:14]=1)([CH3:12])[CH2:9][CH2:10][CH3:11].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[BH3-]C#N.[Na+]>ClCCl.CN(C=O)C>[CH3:12][C:8]([C:13]1[S:17][C:16]([NH:18][C:19](=[O:25])[CH:20]([NH:24][CH:3]([CH2:4][CH3:5])[CH2:2][CH3:1])[CH2:21][CH2:22][CH3:23])=[N:15][N:14]=1)([CH3:7])[CH2:9][CH2:10][CH3:11]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 7288Ethyl ketoneHCID 5003444Sodium cyanoborohydrideHCID 5049666Sodium triacetoxyborohydrideHCID 86033134HCID 86033134, compound

Product 1

HCID 85432458HCID 85432458, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of pentan-3-one (0.3 mmol), 2-Amino-pentanoic acid [5-(1,1-dimethyl-butyl)-[1,3,4]thiadiazol-2-yl]-amide (0.3 mmol), sodium triacetoxy borohydride (0.3 mmol) and acetic acid (0.3 mmol) in 1.0 mL of anhydrous dichloromethane and 1 ml DMF was stirred at room temperature (rt) overnight. The reaction was not complete. The mixture was treated with NaBH3CN (40 mg) and heated at 45° C. for 4 hr. All starting material was consumed. The crude solution was diluted with dilute NaOH and extracted with methylene chloride. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude products were purified through Shimadzu HPLC to give 2-(1-Ethyl-propylamino)-pentanoic acid [5-(1,1-dimethyl-butyl)-[1,3,4]thiadiazol-2-yl]-amide. LC-MS (retention time, M+1): 1.70 min, 355.3 [M+1]

Workup

  1. temperatureheated at 45° C. for 4 hr
  2. customwas consumed
  3. additionThe crude solution was diluted with dilute NaOH
  4. extractionextracted with methylene chloride
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude products were purified through Shimadzu HPLC

Sources & evidence

ORD record
ord-2a4fed598a904889a63273a02704b9e2
Source dataset
uspto-grants-2007_06
Patent number
US07232820B2

Reaction notes

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