Water → HCID 22490258, compound

HRID 2180018Notes

Reaction equation

HRID 2180018 reaction equation
CS(O[CH:6]([CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=1)[CH2:7][NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])(=O)=O.C(Cl)Cl.[OH-].[Na+].O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.CCOCC>[C:27]([C:24]1[CH:25]=[CH:26][C:21]([O:20][CH2:19][CH:6]2[CH2:7][N:8]2[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])=[CH:22][CH:23]=1)#[N:28]

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 22490282HCID 22490282, compound

Product 1

HCID 22490258HCID 22490258, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

2-{[(Benzyloxy)carbonyl]amino}-1-[(4-cyanophenoxy)methyl]ethyl methanesulfonate (47.7 mg; 0.12 mol; from step (ii) above), tetrabutylammonium hydrogensulfate (4.81 g; 0.014 mol) and 290 mL of DCM were mixed and cooled to 0° C. 97 mL of 50% NaOH was added and the mixture was stirred vigorously for 50 minutes. 500 mL of water and 500 mL of ether were added. The organic phase was separated, washed with water, dried (Na2SO4) and evaporated. Purification by chromatography on silica (DCM) gave 33.13 g (89%) of the sub-title compound.

Workup

  1. customThe organic phase was separated
  2. washwashed with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customPurification by chromatography on silica (DCM)

Sources & evidence

ORD record
ord-f195e737c66f4426a5ef096478a51bf4
Source dataset
uspto-grants-2005_05
Patent number
US06887881B1

Reaction notes

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