Cyclopropyl methyl ketone → HCID 11688150, compound

HRID 131658Notes

Reaction equation

HRID 131658 reaction equation
[CH:1]([C:4]1[S:8][C:7]([NH:9][C:10](=[O:16])[C@@H:11]([NH2:15])[CH2:12][CH2:13][CH3:14])=[N:6][CH:5]=1)([CH3:3])[CH3:2].[CH3:17][C:18]([CH:20]1[CH2:22][CH2:21]1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[CH:1]([C:4]1[S:8][C:7]([NH:9][C:10](=[O:16])[C@@H:11]([NH:15][CH:18]([CH:20]2[CH2:22][CH2:21]2)[CH3:17])[CH2:12][CH2:13][CH3:14])=[N:6][CH:5]=1)([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 13004Cyclopropyl methyl ketoneHCID 5049666Sodium triacetoxyborohydrideHCID 866045872-(S)-amino-pentanoic acid (5-isopropyl-thiazol-2-yl)amide

Product 1

HCID 11688150HCID 11688150, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(S)-amino-pentanoic acid (5-isopropyl-thiazol-2-yl)-amide (150 mg, 0.54 mmol) and cyclopropyl methyl ketone(45 mg, 0.54 mmol)in 10 mL of methylene chloride and 5 drops of acetic acid was treated with sodium triacetoxyborohydride (172 mg, 0.8 mmol) and stirred at room temperature overnight. The mixture was quenched with dilute ammonium hydroxide and extracted with methylene chloride. The organic layer was separated and concentrated to dryness. The residue was purified by HPLC to give 2-(S)-(1-cyclopropyl-ethylamino)-pentanoic acid (5-isopropyl-thiazol-2-yl)-amide as a colorless oil, LC-MS RT=1.4 min, M+1=310.

Workup

  1. customThe mixture was quenched with dilute ammonium hydroxide
  2. extractionextracted with methylene chloride
  3. customThe organic layer was separated
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-72f956fc39ee401983bf751b1dfa1351
Source dataset
uspto-grants-2008_06
Patent number
US07384968B2

Reaction notes

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