HCID 86760908, compound → HCID 86760907, compound

HRID 1988282Notes

Reaction equation

HRID 1988282 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH:13]([NH:19][C:20](=[O:44])[CH:21]([NH:25][CH2:26][CH:27]([NH:36]C(OC(C)(C)C)=O)[CH2:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[CH:22]([CH3:24])[CH3:23])[C:14]2[S:15][CH:16]=[CH:17][N:18]=2)[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH:13]([NH:19][C:20](=[O:44])[CH:21]([NH:25][CH2:26][CH:27]([NH2:36])[CH2:28][C:29]2[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=2)[CH:22]([CH3:24])[CH3:23])[C:14]2[S:15][CH:16]=[CH:17][N:18]=2)[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 86760908HCID 86760908, compound

Product 1

HCID 86760907HCID 86760907, compoundYield 71.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 2-[2-tert-butoxycarbonylamino-3-(4-fluorophenyl)propyl]amino-3-methylbutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(thiazol-2-yl)ethylamide (A) (300 mg) in methylene chloride (5 ml), TFA (1 ml) was added under cooling with ice. The mixture was stirred at room temperature for 1 hour and evaporated under reduced pressure; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: methylene chloride:methanol=15:1), giving the titled compound (180 mg, 71%).

Workup

  1. temperatureunder cooling with ice
  2. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-aafebca6bfd1401d8213009c7f8123f6
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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