Dichloromethane → H-Thz-NH-tBu

HRID 263661Notes

Reaction equation

HRID 263661 reaction equation
[N:1]1(C(OC(C)(C)C)=O)[CH2:12][S:11][CH2:10][C@H:2]1[C:3]([NH:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].CS(O)(=O)=O.ClCCl.[OH-].[Na+]>C(#N)C.ClCCl>[NH:1]1[CH2:12][S:11][CH2:10][C@H:2]1[C:3]([NH:5][C:6]([CH3:9])([CH3:7])[CH3:8])=[O:4]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 54130109HCID 54130109, compound

Product 1

HCID 10535636H-Thz-NH-tBuYield 88%

Reagents, catalysts & solvents 1

HCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

To a solution of 5.00 g (17.4 mmol) of Boc-Thz-NH-tBu in 23.7 ml of acetonitrile-dichloromethane (1:6), 3.39 ml (52.1 mmol) of methanesulfonic acid was added. After stirring at room temperature for 1.5 h, 30 ml of dichloromethane and 26 ml (52 mmol) of 2N NaOH aqueous solution were added under ice cooling to extract the product. The organic layer was washed with 5% NaHCO3 aqueous solution and saturated NaCl aqueous solution successively, dried over Na2SO4, and evaporated under reduced pressure. The residue was triturated in 50 ml of hexane to give 2.86 g (Y. 88%) of H-Thz-NH-tBu which was converted to Qoa-Mta-AHPBA-Thz-NH-tBu by a similar method with processes 3-5 of Example 3.

Workup

  1. extractionto extract the product
  2. washThe organic layer was washed with 5% NaHCO3 aqueous solution and saturated NaCl aqueous solution successively
  3. dry with materialdried over Na2SO4
  4. customevaporated under reduced pressure
  5. customThe residue was triturated in 50 ml of hexane

Sources & evidence

ORD record
ord-ca11e0de0ba743759c041a847e9bfb9c
Source dataset
uspto-grants-1997_07
Patent number
US05644028

Reaction notes

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