Methanol → HCID 20695532, compound

HRID 380795Notes

Reaction equation

HRID 380795 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[CH:4][C:3]=1[N:22]=[C:23]1[N:27]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:26](=[O:34])[CH:25]([CH2:35][C:36](=[O:58])[NH:37][O:38]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[S:24]1.C([SiH](C(C)C)C(C)C)(C)C.CO>FC(F)(F)C(O)=O.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:17])[F:18])[N:11]([CH3:20])[C:10]2=[O:21])=[CH:4][C:3]=1[N:22]=[C:23]1[N:27]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:26](=[O:34])[CH:25]([CH2:35][C:36](=[O:58])[NH:37][OH:38])[S:24]1

Participants

6

Reactant 3

HCID 887MethanolHCID 138754Silane, tris(1-methylethyl)-HCID 86585964HCID 86585964, compound

Product 1

HCID 20695532HCID 20695532, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of ethyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-5-{[(trityloxy)carbamoyl]-methyl}-3-thiazolidineacetate (entire sample from Example 23) and triisopropylsilane (1 mL) in trifluoroacetic acid (19 mL) is stirred at room temperature for 4 hours, cooled with an ice-water bath, and filtered. The resultant filtrate is concentrated in vacuo and chased three times with toluene to obtain a solid. Column chromatography of the solid using silica gel and a 7.5% methanol in methylene chloride solution gives the title product as a yellow solid which is identified by 1H NMR spectral analysis.

Workup

  1. temperaturecooled with an ice-water bath
  2. filtrationfiltered
  3. concentrationThe resultant filtrate is concentrated in vacuo
  4. customto obtain a solid

Sources & evidence

ORD record
ord-0413268f571d4b69a0a302f038bb4f70
Source dataset
uspto-grants-2001_10
Patent number
US06303783B1

Reaction notes

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