Water → HCID 66671463, compound

HRID 446610Notes

Reaction equation

HRID 446610 reaction equation
[C:1]1([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:43])[O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]([C:20](=[O:42])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]2[CH:32]=[CH:31][C:30]([N:33]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH3:34])=[CH:29][CH:28]=2)[CH3:19])[CH2:12][CH2:11]1.[H-].[Na+].Cl[C:53]([O:55][CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)=[O:54].O>O1CCCC1.C(OCC)(=O)C>[C:1]1([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]([CH3:19])[C:20](=[O:42])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([C:27]2[CH:28]=[CH:29][C:30]([N:33]([C:35]([O:37][C:38]([CH3:41])([CH3:39])[CH3:40])=[O:36])[CH3:34])=[CH:31][CH:32]=2)[C:53](=[O:54])[O:55][CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH2:12][CH2:11]1)=[O:43]

Participants

7

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 24758Sodium hydrideHCID 66671689HCID 66671689, compound

Product 1

HCID 66671463HCID 66671463, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound (593 mg, 0.883 mmol) obtained in Example 97a was dissolved in tetrahydrofuran (9 mL), 55% sodium hydride (42 mg, 0.971 mmol) was added under ice cooling, and the mixture was stirred under ice cooling under a nitrogen atmosphere for 15 minutes. Subsequently, benzyl chloroformate (0.19 mL, 1.32 mmol) was added, and the mixture was stirred at room temperature for 18 hours. After the reaction was completed, water was added, and ethyl acetate was further added to separate the layers. The resulting organic layer was separated, washed with saturated sodium chloride solution, and then dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by NH silica gel column chromatography (hexane:ethyl acetate, 1:5→1:15, v/v) to give the title compound (660 mg; yield, 93%) as a colorless oily substance.

Workup

  1. stirringthe mixture was stirred at room temperature for 18 hours
  2. customto separate the layers
  3. customThe resulting organic layer was separated
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by NH silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-c115bacbca5b416aa2a04c63512f94e8
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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