Water → HCID 70295782, compound

HRID 1106909Notes

Reaction equation

HRID 1106909 reaction equation
[CH:1]1[O:2][CH:3]=[C:4]2[C:9]([CH2:10][C:11]([N:13]([CH:15]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([OH:36])[CH:31]=3)[CH2:16][CH:17]3[CH2:21][CH2:20][CH:19]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH2:18]3)[CH3:14])=[O:12])=[CH:8][CH:7]=[CH:6][C:5]=12.C(=O)([O-])[O-].[K+].[K+].[C:43]([O:47][C:48](=[O:51])[CH2:49]Br)([CH3:46])([CH3:45])[CH3:44].O>CN(C)C=O>[C:43]([O:47][C:48](=[O:51])[CH2:49][O:36][C:32]1[CH:33]=[CH:34][CH:35]=[C:30]([CH:15]([N:13]([C:11](=[O:12])[CH2:10][C:9]2[C:4]3[CH:5]=[CH:1][O:2][C:3]=3[CH:6]=[CH:7][CH:8]=2)[CH3:14])[CH2:16][CH:17]2[CH2:21][CH2:20][CH:19]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH2:18]2)[CH:31]=1)([CH3:46])([CH3:45])[CH3:44]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 70295906HCID 70295906, compound

Product 1

HCID 70295782HCID 70295782, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 35 1.63 g, 3.2 mmol) in dimethylformamide (22 mL) was added potassium carbonate (1.37 g, 9.9 mmol) and, under argon, t-butylbromoacetate (0.47 mL, 3.2 mmol). After stirring at room temperature for 23 hours, the reaction was poured into water (160 mL), extracted with dichloromethane (160 mL), dried (MgSO4), and the solvent removed in vacuo. Purification by column chromatography (dichloromethane:methanol 39:1 followed by ethyl acetate:heptane 4:1) gave the product as a clear oil, 1.4 mmol, 45%.

Workup

  1. extractionextracted with dichloromethane (160 mL)
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customPurification by column chromatography (dichloromethane:methanol 39:1 followed by ethyl acetate:heptane 4:1)

Sources & evidence

ORD record
ord-bee9a42a8e1f4134ac38c004fb02aedc
Source dataset
uspto-grants-2000_05
Patent number
US06057357

Reaction notes

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