Benzyl Bromide → Benzyl ((6S,8S)-6-(anilinocarbonyl)-3-{[(benzyloxy)carbonyl][3-(trifluoromethyl)benzyl]amino}-8-methyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-8-yl)acetate

HRID 481257Notes

Reaction equation

HRID 481257 reaction equation
[NH:1]([C:8]([C@H:10]1[N:14]2[C:15](=[O:41])[C:16]([N:19]([C:31]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:32])[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)=[CH:17][N:18]=[C:13]2[C@@:12]([CH2:43][C:44]([OH:46])=[O:45])([CH3:42])[CH2:11]1)=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH:53]1[CH:58]=[CH:57][C:56]([CH2:59]Br)=[CH:55][CH:54]=1>CN(C=O)C.CCOC(C)=O>[NH:1]([C:8]([C@H:10]1[N:14]2[C:15](=[O:41])[C:16]([N:19]([C:31]([O:33][CH2:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[O:32])[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)=[CH:17][N:18]=[C:13]2[C@@:12]([CH2:43][C:44]([O:46][CH2:59][C:56]2[CH:57]=[CH:58][CH:53]=[CH:54][CH:55]=2)=[O:45])([CH3:42])[CH2:11]1)=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 69972821((6S,8S)-6-(Anilinocarbonyl)-3-{[(benzyloxy)carbonyl][3-(trifluoromethyl)benzyl]amino}-8-methyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-8-yl)acetic acid

Product 1

HCID 86587577Benzyl ((6S,8S)-6-(anilinocarbonyl)-3-{[(benzyloxy)carbonyl][3-(trifluoromethyl)benzyl]amino}-8-methyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-8-yl)acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 117b (1.740 mmol) in 7 mL DMF, were added Cs2CO3 (850 mg, 2.61 mmol) and BnBr (0.31 mL, 2.61 mmol). The mixture was stirred at rt for 1 h, then diluted with EtOAc. The organic phase was washed with 0.5 N HCl and brine, dried (Na2SO4), and concentrated. The crude product was purified by flash chromatography (35% EtOAc/hexanes) to afford 533 mg (42%, 2 steps) of 117c as a colorless glass. MS(ESI) 725.3 (M+H+).

Workup

  1. washThe organic phase was washed with 0.5 N HCl and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography (35% EtOAc/hexanes)

Sources & evidence

ORD record
ord-5ca2a9fee6114bfa8ae97f1f9aa291dd
Source dataset
uspto-grants-2003_11
Patent number
US06653295B2

Reaction notes

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