Cesium carbonate → HCID 131726121, compound

HRID 2112318Notes

Reaction equation

HRID 2112318 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]3[O:63][CH2:64]Cl)[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](O)=O)=[O:72])([CH3:69])([CH3:68])[CH3:67].C([O-])([O-])=[O:81].[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:63][C:64](=[O:81])[CH2:77][CH2:76][CH2:75][CH2:74][NH:73][C:71]([O:70][C:66]([CH3:69])([CH3:68])[CH3:67])=[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 131726121HCID 131726121, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound of Example 8B is dissolved in DMF; 4-tert-butoxycarbonylamino-butanoic 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-85fb1667ba9241c6aaf111077250866a
Source dataset
uspto-grants-2009_04
Patent number
US07521439B2

Reaction notes

Loading…