Water → HCID 10310667, compound

HRID 2250820Notes

Reaction equation

HRID 2250820 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][C@@H:27]([CH3:55])[C@H:28]([N:47]1[CH:51]=[C:50]([C:52]([NH2:54])=[O:53])[N:49]=[CH:48]1)[CH2:29][CH2:30][C:31]1[C:36]2[N:37]=[C:38]([C:40]3[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=3)[O:39][C:35]=2[CH:34]=[CH:33][CH:32]=1)(C(C)(C)C)(C)C.CCOC(C)=O.O>C1COCC1>[ClH:46].[OH:26][C@@H:27]([CH3:55])[C@H:28]([N:47]1[CH:51]=[C:50]([C:52]([NH2:54])=[O:53])[N:49]=[CH:48]1)[CH2:29][CH2:30][C:31]1[C:36]2[N:37]=[C:38]([C:40]3[CH:41]=[CH:42][C:43]([Cl:46])=[CH:44][CH:45]=3)[O:39][C:35]=2[CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 11318674HCID 11318674, compound

Product 1

HCID 10310667HCID 10310667, compoundYield 116%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1M solution of tetrabutylammonium fluoride in THF (0.387 ml) was added to a solution of 1-{(3R,4S)-4-(tert-butyldimethylsilyloxy)-1-[2-(4-chlorophenyl)-4-benzoxazolyl]-3-pentyl}imidazole-4-carboxamide (E0001; 0.16 g) in THF (7 ml) and the mixture was stirred at r.t. for 2 hours. EtOAc and water were added and the organic layer was separated, washed with water, dried and evaporated. The residue (0.16 g) was chromatographed over silica gel (5 g) eluting with a mixture of dichloromethane and methanol (20:1 to 10:1). The desired product was treated with HCl in EtOAc to give a white powder of 1-{(3R,4S)-4-hydroxy-1-[2-(4-chlorophenyl)-4-benzoxazolyl]-3-pentyl}imidazole-4-carboxamide hydrochloride (E0017; 79.4 mg).

Workup

  1. customthe organic layer was separated
  2. washwashed with water
  3. customdried
  4. customevaporated
  5. customThe residue (0.16 g) was chromatographed over silica gel (5 g)
  6. washeluting with a mixture of dichloromethane and methanol (20:1 to 10:1)
  7. additionThe desired product was treated with HCl in EtOAc

Sources & evidence

ORD record
ord-e82ab3d8bcc545f286e93d71dff8acde
Source dataset
uspto-grants-2008_01
Patent number
US07317107B2

Reaction notes

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