Cesium carbonate → HCID 131726120, compound

HRID 724555Notes

Reaction equation

HRID 724555 reaction equation
[CH3:1][CH:2]([CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][C@@H:25]2[OH:28])[C@:21]2([CH3:22])[C@@H:16]([CH2:17][C@@H:18]([O:29][CH2:30][CH2:31][N:32]([C:34]4[CH:39]=[CH:38][C:37]([C@H:40]5[CH2:57][C@@:55]6([CH3:56])[C@@H:51]([CH2:52][CH2:53][C@:54]6([OH:61])[C:58]#[C:59][CH3:60])[C@H:50]6[C:41]5=[C:42]5[C:47]([CH2:48][CH2:49]6)=[CH:46][C:45](=[O:62])[CH2:44][CH2:43]5)=[CH:36][CH:35]=4)[CH3:33])[CH2:19][CH2:20]2)[CH2:15][C@H:14]3OCCl)[CH2:11][CH2:10]1)[CH3:8])[C:3]([OH:5])=[O:4].[C:66]([O:70][C:71]([NH:73][CH2:74][CH2:75][CH2:76][C:77]([OH:79])=[O:78])=[O:72])([CH3:69])([CH3:68])[CH3:67].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:1][CH:2]([CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][C@@H:25]2[OH:28])[C@:21]2([CH3:22])[C@@H:16]([CH2:17][C@@H:18]([O:29][CH2:30][CH2:31][N:32]([C:34]4[CH:39]=[CH:38][C:37]([C@H:40]5[CH2:57][C@@:55]6([CH3:56])[C@@H:51]([CH2:52][CH2:53][C@:54]6([OH:61])[C:58]#[C:59][CH3:60])[C@H:50]6[C:41]5=[C:42]5[C:47]([CH2:48][CH2:49]6)=[CH:46][C:45](=[O:62])[CH2:44][CH2:43]5)=[CH:36][CH:35]=4)[CH3:33])[CH2:19][CH2:20]2)[CH2:15][C@H:14]3[O:78][C:77](=[O:79])[CH2:76][CH2:75][CH2:74][NH:73][C:71]([O:70][C:66]([CH3:69])([CH3:67])[CH3:68])=[O:72])[CH2:11][CH2:10]1)[CH3:8])[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2948944-(((Tert-butoxy)carbonyl)amino)butanoic acidHCID 131726119HCID 131726119, compound

Product 1

HCID 131726120HCID 131726120, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound of Example 8B is dissolved in DMF; 4-tert-butoxycarbonylaminobutanoic acid (1.3 eq) is added, along with 1.2 equivalents of Cs2CO3. The resultant mixture is stirred overnight at ambient temperature. The reaction mixture is partitioned between aqueous phosphoric acid (1N) and ethyl acetate. The organic extract is dried (Na2SO4), filtered, and concentrated in vacuo. The crude material is purified on silica gel using a gradient of ethyl acetate in hexanes to provide the title compound.

Workup

  1. customThe reaction mixture is partitioned between aqueous phosphoric acid (1N) and ethyl acetate
  2. extractionThe organic extract
  3. dry with materialis dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material is purified on silica gel using a gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-db7543a46fd8411f83adc2872b375513
Source dataset
uspto-grants-2006_11
Patent number
US07141559B2

Reaction notes

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