Ethyl ketone → HCID 11709849, compound

HRID 131654Notes

Reaction equation

HRID 131654 reaction equation
[CH2:1]([CH:3]([C:6]1[S:10][C:9]([NH:11][C:12](=[O:18])[C@@H:13]([NH2:17])[CH2:14][CH2:15][CH3:16])=[N:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2].[CH3:19][CH2:20][C:21](=O)[CH2:22][CH3:23].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[CH2:1]([CH:3]([C:6]1[S:10][C:9]([NH:11][C:12](=[O:18])[C@@H:13]([NH:17][CH:21]([CH2:22][CH3:23])[CH2:20][CH3:19])[CH2:14][CH2:15][CH3:16])=[N:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2]

Participants

6

Reactant 3

HCID 7288Ethyl ketoneHCID 5049666Sodium triacetoxyborohydride2×HCID 86604588HCID 86604588, compound

Product 1

HCID 11709849HCID 11709849, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(S)-amino-pentanoic acid [5-(1-ethyl-propyl)-thiazol-2-yl]-amide (107 mg, 0.4 mmol) and 3-pentanone (34 mg, 0.4 mmol)in 3 mL of methylene chloride and 5 drops of acetic acid was treated with sodium triacetoxyborohydride (131 mg, 0.62 mmol) and stirred at room temperature overnight. An additional sodium triacetoxyborohydride (167 mg)was added and the resulting mixture was stirred at room temperature for 4 hrs. The mixture was quenched with ammonium hydroxide/water and extracted with methylene chloride. The organic layer was separated, dried, filtered and concentrated to dryness to give a yellow oil. The oil was purified by Shimadzu HPLC to give 2-(S)-(1-Ethyl-propylamino)-pentanoic acid [5-(1-ethyl-propyl)-thiazol-2-yl]-amide as a colorless oil, RT=1.88 min, M+1=340.4.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 4 hrs
  2. customThe mixture was quenched with ammonium hydroxide/water
  3. extractionextracted with methylene chloride
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customto give a yellow oil
  9. customThe oil was purified by Shimadzu HPLC

Sources & evidence

ORD record
ord-13e6d62b10f04746ba8e9e377b53c41b
Source dataset
uspto-grants-2008_06
Patent number
US07384968B2

Reaction notes

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