Trifluoroacetic acid → HCID 53328064, compound

HRID 446831Notes

Reaction equation

HRID 446831 reaction equation
[F:1][C@H:2]1[CH2:18][C@@H:17]2[C@:9]([F:25])([C@@H:10]([OH:24])[CH2:11][C@@:12]3([CH3:23])[C@H:16]2[CH2:15][CH:14]=[C:13]3[C:19](=[O:22])[CH2:20][OH:21])[C@:8]2([CH3:26])[C:3]1=[CH:4][C:5](=[O:27])[CH:6]=[CH:7]2.[CH2:28]([N:35]([CH2:39][Si](C)(C)C)[CH2:36]OC)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C1(C)C(C)=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl.C(Cl)Cl.CCOC(C)=O>[CH2:28]([N:35]1[CH2:39][C@:13]2([C:19](=[O:22])[CH2:20][OH:21])[C@@H:14]([CH2:15][C@H:16]3[C@H:17]4[C@@:9]([F:25])([C@:8]5([CH3:26])[C:3]([C@@H:2]([F:1])[CH2:18]4)=[CH:4][C:5](=[O:27])[CH:6]=[CH:7]5)[C@@H:10]([OH:24])[CH2:11][C@@:12]32[CH3:23])[CH2:36]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7237O-XyleneHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 58187768HCID 58187768, compound

Product 1

HCID 53328064HCID 53328064, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226138Dichloromethane ethylacetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of intermediate 6 (95 mg, 0.185 mmol), N-benzyl-1-methoxy-N-((trimethylsilyl)methyl)methanamine (500 mg) and then Xylene (5 ml) containing 0.01% of TFA is placed in a closed vessel and heated at 140° C. for 1 hour. The solvent is removed under vacuum, and the residue is purified by silica gel cartridge eluting with DCM to DCM:AcOEt 6:4 leading to the title compound (52 mg, 0.102 mmol, 54.9% yield).

Workup

  1. customis placed in a closed vessel
  2. customThe solvent is removed under vacuum
  3. customthe residue is purified by silica gel cartridge

Sources & evidence

ORD record
ord-9821ccdc260a425d88db5271ec75b9fa
Source dataset
uspto-grants-2013_07
Patent number
US08481517B2

Reaction notes

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