Diisopropylethylamine → 5-(2-tert-Butoxycarbonylamino-ethylcarbamoyl)-1H-indole-2-carboxylic acid pentafluorophenyl ester

HRID 724516Notes

Reaction equation

HRID 724516 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18]([C:23]([OH:25])=[O:24])=[CH:17]2)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.FC(F)(F)C(O[C:40]1[C:45]([F:46])=[C:44]([F:47])[C:43]([F:48])=[C:42]([F:49])[C:41]=1[F:50])=O>CN(C=O)C>[F:46][C:45]1[C:40]([O:24][C:23]([C:18]2[NH:19][C:20]3[C:16]([CH:17]=2)=[CH:15][C:14]([C:12](=[O:13])[NH:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[CH:22][CH:21]=3)=[O:25])=[C:41]([F:50])[C:42]([F:49])=[C:43]([F:48])[C:44]=1[F:47]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 587470885-(2-tert-Butoxycarbonylamino-ethylcarbamoyl)-1H-indole-2-carboxylic acid

Product 1

HCID 865916045-(2-tert-Butoxycarbonylamino-ethylcarbamoyl)-1H-indole-2-carboxylic acid pentafluorophenyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound 32 (0.154 g, 0.44 μmol) in DMF (5 mL) in the presence of DIEA (93 ml, 0.53 mmol) was added dropwise pentafluorophenyl trifluoroacetate (92 μl, 0.53 mmol) at 0° C. The resulting reaction mixture was stirred at room temperature overnight. HPLC showed that the reaction was completed. The solvent was then evaporated to dryness, and the residue was carefully washed with ether to give compound 33 in quantitative yield.

Workup

  1. customThe resulting reaction mixture
  2. customThe solvent was then evaporated to dryness
  3. washthe residue was carefully washed with ether

Sources & evidence

ORD record
ord-b120770e038845eb9f3d0ddbdbacb8ff
Source dataset
uspto-grants-2006_11
Patent number
US07141680B2

Reaction notes

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