Dimethylformamide → HCID 77311070, compound

HRID 1392064Notes

Reaction equation

HRID 1392064 reaction equation
[CH:1]1([CH2:4][CH:5]([CH:9]([OH:14])[CH2:10][CH2:11][CH2:12][CH3:13])[C:6]([OH:8])=O)[CH2:3][CH2:2]1.CN(C(ON1N=[N:30][C:25]2[CH:26]=[CH:27][CH:28]=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C[N:40]1[CH2:45][CH2:44]O[CH2:42][CH2:41]1.[CH3:46][N:47]([CH:49]=[O:50])[CH3:48]>O>[O:50]=[C:49]1[CH:25]([NH:30][C:6](=[O:8])[CH:5]([CH2:4][CH:1]2[CH2:2][CH2:3]2)[CH:9]([OH:14])[CH2:10][CH2:11][CH2:12][CH3:13])[CH2:26][CH2:27][CH2:28][CH2:46][N:47]1[CH2:48][C:1]1[CH:2]=[CH:3][CH:44]=[C:45]([NH:40][C:41]2[CH:42]=[CH:10][CH:9]=[CH:5][CH:6]=2)[CH:4]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 21941494HCID 21941494, compound

Product 1

HCID 77311070HCID 77311070, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 25 mL round bottomed flask 2-Cyclopropylmethyl-3-hydroxy-heptanoic acid (0.0125 g, 0.061 mmol) was dissolved in 1 mL DMF. To the reaction mixture HATU, O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate, (0.029 g, 0.0734 mmol) and N-Methyl morpholine (0.018 g, 0.018 mmol) were added and the reaction solution was stirred at room temperature for 10 minutes. To the reaction mixture the compound from Step 2 above (0.025 g, 0.06 mmol) dissolved in 1 mL of DMF was added and the reaction solution was stirred at room temperature for 18 h. The solution was diluted with 50 mL of water and extracted twice with 20 mL of ethyl acetate. The combined organic layers were dried with anhydrous Sodium sulfate, filtered, and concentrated to an oil. The oil was purified on a flash silica gel column using 20-40% ethyl acetate in hexanes as eluent to yield 6.0 mg (20%). MS (ESI) M+H=492.6

Workup

  1. additionwas added
  2. stirringthe reaction solution was stirred at room temperature for 18 h
  3. extractionextracted twice with 20 mL of ethyl acetate
  4. dry with materialThe combined organic layers were dried with anhydrous Sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. customThe oil was purified on a flash silica gel column
  8. customto yield 6.0 mg (20%)

Sources & evidence

ORD record
ord-c83b097df83b47f798c9c1d7457ea1a4
Source dataset
uspto-grants-2008_03
Patent number
US07342008B2

Reaction notes

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