Cornforth reagent → HCID 86695112, compound

HRID 1503939Notes

Reaction equation

HRID 1503939 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][O:5][CH2:6][C@H:7]1[CH2:18][CH2:17][C:16]2[S:15][C:14]3[N:13]=[CH:12][N:11]=[C:10]([O:19][CH:20]4[CH2:25][CH2:24][CH:23]([N:26]([CH3:34])[C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:22][CH2:21]4)[C:9]=3[C:8]1=2.C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-:47][Cr](O[Cr]([O-])(=O)=O)(=O)=O>CN(C=O)C>[C:29]([O:28][C:27]([N:26]([CH3:34])[CH:23]1[CH2:22][CH2:21][CH:20]([O:19][C:10]2[C:9]3[C:8]4[C@@H:7]([CH2:6][O:5][CH2:4][CH2:3][C:2]([OH:47])=[O:1])[CH2:18][CH2:17][C:16]=4[S:15][C:14]=3[N:13]=[CH:12][N:11]=2)[CH2:25][CH2:24]1)=[O:33])([CH3:31])([CH3:30])[CH3:32]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 86695113HCID 86695113, compound

Product 1

HCID 86695112HCID 86695112, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A 50-mL round-bottom flask was charged with a solution of tert-butyl N-(4-[[(3S)-3-[(3-hydroxypropoxy)methyl]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate (370 mg, 0.75 mmol, 1.00 equiv) in 5 mL of DMF and PDC (1.656 g, 4.40 mmol, 5.85 equiv) was added at room temperature. The resulting solution was stirred for 14 hrs at 25° C. After completion, the resulting solution was extracted with 3×50 mL of ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:2) to give 3-[[(3S)-12-[(4-[[(tert-butoxy)carbonyl](methyl)amino]cyclohexyl)oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]methoxy]propanoic acid (190 mg, 50%) as a colorless oil. MS: m/z 492 (M+H)+.

Workup

  1. additionwas added at room temperature
  2. extractionAfter completion, the resulting solution was extracted with 3×50 mL of ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a4dbff5dde5d40e698aeb3f681e22bf2
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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