Acetic Anhydride → HCID 57439883, compound

HRID 906036Notes

Reaction equation

HRID 906036 reaction equation
[CH3:1]CN(CC)CC.[CH3:8][C:9]([O:11][C:12]([CH3:14])=[O:13])=O.OC1C=[CH:20][C:19]([NH:22][C:23]([C:25]2[CH:30]=[CH:29][C:28]([N:31]3[CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33][CH2:32]3)=[CH:27][CH:26]=2)=O)=[CH:18][CH:17]=1>C(Cl)Cl>[C:12]([O:11][C:9]1[CH:17]=[CH:18][C:19]([NH:22][C:23]([C:25]2[CH:30]=[CH:29][C:28]([N:31]3[CH2:32][CH2:33][N:34]([C:37]([O:39][C:40]([CH3:41])([CH3:43])[CH3:42])=[O:38])[CH2:35][CH2:36]3)=[CH:27][CH:26]=2)=[CH2:1])=[CH:20][CH:8]=1)(=[O:13])[CH3:14]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 11516825Tert-butyl 4-[4-[(4-hydroxyphenyl)carbamoyl]phenyl]piperazine-1-carboxylate

Product 1

HCID 57439883HCID 57439883, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.1 eq of Et3N and 2 eq of Ac2O were added to a solution of tert-butyl 4-(4-{[(4-hydroxyphenyl)amino]carbonyl}phenyl)piperazine-1-carboxylate in dry DCM (0.1 M) (prepared as described in published International patent application WO98/00134) and the solution stirred at RT for 16 h under a nitrogen atmosphere. The reaction mixture was diluted with DCM and the organic phase was washed with aqueous HCl (1N) (twice), saturated aqueous NaHCO3 and then brine. The organic phase was dried over Na2SO4, filtered and the solvent evaporated in vacuo to afford the title compound as a white solid (90%); MS (ES+) m/z 440 (M+H)+

Workup

  1. washthe organic phase was washed with aqueous HCl (1N) (twice), saturated aqueous NaHCO3
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-744a580611014449bdbdc175e2c4a140
Source dataset
uspto-grants-2011_09
Patent number
US08012982B2

Reaction notes

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