Acetic Acid → n-((1s,2r)-1-((4-Chlorophenyl)methyl)-3-(((4's)-6'-(2,2-dimethylbutyl)-3',4'-dihydrospiro[cyclobutane-1,2'-pyrano[2,3-b]pyridin]-4'-yl)amino)-2-hydroxypropyl)acetamide

HRID 1009133Notes

Reaction equation

HRID 1009133 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([NH:33][C:34](=[O:36])[CH3:35])[C@H:10]([OH:32])[CH2:11][NH:12][C@@H:13]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([CH2:23][C:24]([CH3:28])([CH3:27])[C:25]#[CH:26])[CH:21]=3)[O:16][C:15]3([CH2:31][CH2:30][CH2:29]3)[CH2:14]2)=[CH:4][CH:3]=1.CC(O)=O>CO.C(O)(N=NC(O)=O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([NH:33][C:34](=[O:36])[CH3:35])[C@H:10]([OH:32])[CH2:11][NH:12][C@@H:13]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([CH2:23][C:24]([CH3:27])([CH3:28])[CH2:25][CH3:26])[CH:21]=3)[O:16][C:15]3([CH2:31][CH2:30][CH2:29]3)[CH2:14]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 176Acetic Acid2×HCID 87349212n-((1s,2r)-1-((4-Chlorophenyl)methyl)-3-(((4's)-6'-(2,2-dimethyl-3-butyn-1-yl)-3',4'-dihydrospiro[cyclobutane-1,2'-pyrano[2,3-b]pyridin]-4'-yl)amino)-2-hydroxypropyl)acetamide

Product 1

HCID 67305464n-((1s,2r)-1-((4-Chlorophenyl)methyl)-3-(((4's)-6'-(2,2-dimethylbutyl)-3',4'-dihydrospiro[cyclobutane-1,2'-pyrano[2,3-b]pyridin]-4'-yl)amino)-2-hydroxypropyl)acetamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 415805Diazenedicarboxylic acidSolvent

Procedure

The compound of Example 492 (0.100 g, 0.196 mmol) was dissolved in MeOH (2 mL) and diazenedicarboxylic acid, dipotassium salt (0.762 g, 3.92 mmol) was added. HOAc (0.673 ml, 11.8 mmol) in MeOH (2 mL) was slowly added to the heterogeneous solution and the reaction was stirred. After all the acetic acid was added and the solution went from yellow to clear and upon complete reduction, the reaction was concentrated and partitioned between 1 N NaOH and DCM. The aqueous was layer was extracted with DCM and the combined organics were washed with brine and concentrated. The crude material was dissolved in a minimal amount of MeOH and directly purified by reverse phase HPLC to afford the title compound. MS m/z: 514.2 (M+1).

Workup

  1. concentrationthe reaction was concentrated
  2. custompartitioned between 1 N NaOH and DCM
  3. extractionwas extracted with DCM
  4. washthe combined organics were washed with brine
  5. concentrationconcentrated
  6. dissolutionThe crude material was dissolved in a minimal amount of MeOH
  7. customdirectly purified by reverse phase HPLC

Sources & evidence

ORD record
ord-1721051cec2d46d08fa6977576cf239e
Source dataset
uspto-grants-2011_07
Patent number
US07973047B2

Reaction notes

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