Water → HCID 66813907, compound

HRID 1099137Notes

Reaction equation

HRID 1099137 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[C:7]([N:26]1[C:30]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:37]2[CH:42]=[CH:41][C:40]([CH2:43][NH:44][C@@H:45]([CH3:48])[CH2:46][OH:47])=[CH:39][CH:38]=2)=[N:29][N:28]=[N:27]1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CCN(C(C)C)C(C)C.O>C1(C)C=CC=CC=1>[OH:47][CH2:46][C@@H:45]([N:44]([CH2:43][C:40]1[CH:39]=[CH:38][C:37]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[C:30]2[N:26]([C:7]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:27]=[N:28][N:29]=2)=[CH:42][CH:41]=1)[C:1](=[O:5])[CH2:2][CH2:3][CH3:4])[CH3:48]

Participants

6

Reactant 4

HCID 962WaterHCID 8855Butyryl chlorideHCID 81531DiisopropylethylamineHCID 66813502HCID 66813502, compound

Product 1

HCID 66813907HCID 66813907, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Butyryl chloride (258 μL, 2.5 mmol) was added to a solution of intermediate (5a) (1.1 g, 2.1 mmol), and DIPEA (504 μL, 2.9 mmol) in toluene (20 mL) at 0° C. The solution was stirred at room temperature for 30 minutes. Water was added (20 mL), and the aqueous phase was extracted with EtOAc (3×30 mL). The combined organic extracts were washed with saturated aqueous NaCl, dried over MgSO4, filtered, and concentrated in vacuo. Silica gel chromatography gave intermediate (5b) as a white solid (942 mg).

Workup

  1. extractionthe aqueous phase was extracted with EtOAc (3×30 mL)
  2. washThe combined organic extracts were washed with saturated aqueous NaCl
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5374f843353b4e6599c6c8ca72bf7683
Source dataset
uspto-grants-2012_03
Patent number
US08143298B2

Reaction notes

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