Water → 3-[[2'-(1-Triphenylmethyltetrazol-5-yl)biphenyl-4-yl]methyloxy]-4-valeramidobenzoic acid morpholide

HRID 2730

Reaction equation

HRID 2730 reaction equation
[C:1]1([C:7]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[N:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]3[CH:24]=[CH:23][C:22]([CH2:25][O:26][C:27]4[CH:28]=[C:29]([CH:38]=[CH:39][C:40]=4[NH2:41])[C:30]([N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)=[O:31])=[CH:21][CH:20]=3)=[N:11][N:10]=[N:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:54](Cl)(=[O:59])[CH2:55][CH2:56][CH2:57][CH3:58].O>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:48]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[N:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]3[CH:20]=[CH:21][C:22]([CH2:25][O:26][C:27]4[CH:28]=[C:29]([CH:38]=[CH:39][C:40]=4[NH:41][C:54](=[O:59])[CH2:55][CH2:56][CH2:57][CH3:58])[C:30]([N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)=[O:31])=[CH:23][CH:24]=3)=[N:11][N:10]=[N:9]2)[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1

Participants

6

Reactant 3

HCID 962WaterHCID 61186Valeryl chlorideHCID 867523143-[[2'-(1-Triphenylmethyltetrazol-5-yl)biphenyl-4-yl]methyloxy]-4-aminobenzoic acid morpholide

Product 1

HCID 867523153-[[2'-(1-Triphenylmethyltetrazol-5-yl)biphenyl-4-yl]methyloxy]-4-valeramidobenzoic acid morpholide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

The compound ([3]-(34)-587) (0.07 g) prepared in Example 38 and 4-dimethylaminopyridine (0.01 g) were dissolved in dry pyridine (1 ml). Valeryl chloride (0.043 g) was added dropwise by a syringe while cooling on ice. The mixture was stirred at room temperature for 2 hours, then, poured into water (20 ml), extracted with chloroform (10 ml) twice, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain the compound ([3]-(35)-587') (0.08 g) as a light yellow solid.

Workup

  1. temperaturewhile cooling on ice
  2. extractionextracted with chloroform (10 ml) twice
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customto obtain the compound ([3]-(35)-587') (0.08 g) as a light yellow solid

Sources & evidence

ORD record
ord-72f20e5a16b14b8398629965aa0bea7a
Source dataset
uspto-grants-1998_03
Patent number
US05731310

Linked notes

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