HCID 18537660, compound → HCID 86587775, compound

HRID 412381Notes

Reaction equation

HRID 412381 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][O:17][C:18]2[CH:19]=[CH:20][C:21]([NH:33][C:34](=O)[CH2:35][O:36][C:37]3[CH:42]=[CH:41][C:40]([CH2:43][CH:44]4[S:48][C:47](=[O:49])[NH:46][C:45]4=[O:50])=[CH:39][CH:38]=3)=[C:22]([N:24](C)[C:25](=O)OC(C)(C)C)[CH:23]=2)=[CH:11][CH:10]=1)=O)(C)(C)C>FC(F)(F)C(O)=O>[NH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][O:17][C:18]2[CH:19]=[CH:20][C:21]3[N:33]=[C:34]([CH2:35][O:36][C:37]4[CH:42]=[CH:41][C:40]([CH2:43][CH:44]5[S:48][C:47](=[O:49])[NH:46][C:45]5=[O:50])=[CH:39][CH:38]=4)[N:24]([CH3:25])[C:22]=3[CH:23]=2)=[CH:13][CH:14]=1

Participants

3

Reactant 1

HCID 18537660HCID 18537660, compound

Product 1

HCID 86587775HCID 86587775, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of t-butyl N-[5-[2-(4-t-butoxycarbonylaminophenyl)ethoxy]-2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetylamino]phenyl]-N-methylcarbamate (18.2 g) in trifluoroacetic acid (100 ml) was stirred at 70° C. for 3.5 hours. The reaction mixture was concentrated, diluted with water, neutralized with sodium bicarbonate and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on a silica gel column using ethyl acetate as the eluant to afford the desired compound (9.2 g, mp 184-188° C.).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-ab3548b44ba14959aa497694d39d1433
Source dataset
uspto-grants-2003_05
Patent number
US06562849B1

Reaction notes

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