Cesium carbonate → HCID 18700179, compound

HRID 2289350Notes

Reaction equation

HRID 2289350 reaction equation
[F:1][C:2]([F:33])([F:32])[CH2:3][O:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:6]=1[CH2:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([N:21]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[CH2:24][O:23][C:22]2=[O:31])[CH2:17][CH2:16]1)=[O:14].Br[CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[F:33][C:2]([F:1])([F:32])[CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH:8]=[CH:7][C:6]=1[CH2:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([N:21]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[CH2:24][O:23][C:22]2=[O:31])[CH2:17][CH2:16]1)=[O:14]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 18700129HCID 18700129, compound

Product 1

HCID 18700179HCID 18700179, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1-(1-(2-(2,2,2-trifluoro-ethoxy)-4-hydroxyphenylacetyl)piperidin-4-yl)-4H-3,1-benzoxazin-2(1H)-one (0.54 g, 1.2 mmol) from Example 32 in DMF (10 mL) was added tert-butyl bromoacetate (0.51 mL, 3.6 mmol) and Cs2CO3 (0.48 g, 1.5 mmol). The mixture was stirred at ambient temperature for 18 h. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc (10 mL) and water (50 mL). The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure to give 1-(1-(2-(2,2,2-trifluoro-ethoxy)-4-(tert-butyloxycarbonylmethoxy)phenylacetyl)piperidin-4-yl)-4H-3,1-benzoxazin-2(1H)-one as a pale yellow oil (HPLC retention time=27.3 min (method D)).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between EtOAc (10 mL) and water (50 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f62311f32b73481f851e499d89787d09
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

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