Water → HCID 59542990, compound

HRID 1876343Notes

Reaction equation

HRID 1876343 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([NH:11][CH:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[CH:10]=1)[NH:7][C:6]([C:18]1[S:19][CH2:20][C@@H:21]([CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[N:22]=1)=[CH:5]2.C(N(C(C)C)CC)(C)C.O=C1CCC(=O)N1[O:47][C:48](=O)[CH2:49][C:50]([F:53])([F:52])[F:51].O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([NH:11][CH:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[CH:10]=1)[NH:7][C:6]([C:18]1[S:19][CH2:20][C@@H:21]([CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][N:28]([C:48](=[O:47])[CH2:49][C:50]([F:53])([F:52])[F:51])[CH2:27][CH2:26]3)[N:22]=1)=[CH:5]2

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 56777211HCID 56777211, compoundHCID 59543060HCID 59543060, compound

Product 1

HCID 59542990HCID 59542990, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (66 mg, 0.15 mmol) prepared in Example 117 was dissolved in dichloromethane (10 ml). Diisopropylethylamine (0.08 ml, 0.44 mmol) and 3,3,3-trifluoropropionic acid 2,5-dioxo-pyrrolidin-1-yl ester (29 mg, 0.13 mmol) were added thereto, and the mixture was stirred for 8 h at room temperature. After completion of the reaction, water was added. The mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and filtered. The filtrate was distilled under reduced pressure, and purified by column chromatography to give the title compound (6 mg, Yield 9%).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationThe filtrate was distilled under reduced pressure
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-f28f650e5c7241519c7380d839a1c5ff
Source dataset
uspto-grants-2012_11
Patent number
US08309586B2

Reaction notes

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