Potassium Carbonate → HCID 86612601, compound

HRID 1784949Notes

Reaction equation

HRID 1784949 reaction equation
[OH:1][CH:2]([CH2:19][NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]#[C:29][Si](C)(C)C)[CH:23]=1)[CH:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.CO>[C:28]([C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[CH2:21][NH:20][CH2:19][CH:2]([OH:1])[CH:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)#[CH:29]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 68958578HCID 68958578, compound

Product 1

HCID 86612601HCID 86612601, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To tert-butyl 3-hydroxy-1-phenyl-4-(3-((trimethylsilyl)ethynyl)benzylamino)butan-2-ylcarbamate in a mixture of THF (2 ml) and MeOH (2 ml), 1M K2CO3 (0.25 ml) was added and the reaction mixture was stirred at rt for 18 h. Then solvent was removed, crude residue was redissolved in ethyl acetate, washed with water, brine and dried. Column purification yielded tert-butyl 4-(3-ethynylbenzylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamate in 85% yield.

Workup

  1. additionwas added
  2. customThen solvent was removed
  3. dissolutioncrude residue was redissolved in ethyl acetate
  4. washwashed with water, brine
  5. customdried
  6. customColumn purification

Sources & evidence

ORD record
ord-62eedefc3d194f2398d7a8f3f0424e2a
Source dataset
uspto-grants-2009_03
Patent number
US07504420B2

Reaction notes

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