Acetone → HCID 58573620, compound

HRID 1048566Notes

Reaction equation

HRID 1048566 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.[NH2:16][C@H:17]([C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)[C@@H:18]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[C:26]([Cl:31])[CH:25]=1)[CH2:19][CH2:20][C:21]([OH:23])=O.[CH3:39][C:40]([CH3:42])=O.ClC(Cl)C>CN(C=O)C>[Cl:31][C:26]1[CH:25]=[C:24]([C@@H:18]2[C@@H:17]([C:32]3[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][CH:37]=3)[N:16]([CH:40]([CH3:42])[CH3:39])[C:21](=[O:23])[CH2:20][CH2:19]2)[CH:29]=[CH:28][C:27]=1[F:30]

Participants

6

Reactant 4

HCID 180AcetoneHCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 67999769HCID 67999769, compound

Product 1

HCID 58573620HCID 58573620, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium triacetoxyborohydride (1.796 g, 8.48 mmol) was added to a solution of (4R,5S)-5-amino-4-(3-chloro-4-fluorophenyl)-5-(4-chlorophenyl)pentanoic acid hydrochloride (2.56 g, 6.52 mmol; Example 390, Step B) and acetone (0.491 mL, 6.68 mmol) in anhydrous DMF (6.52 mL) at rt. The reaction mixture was stirred at rt for 16 hours. Dichloroethane (25 mL) was added followed by 3 Å molecular sieves. The reaction mixture was heated to 70° C. for 22 hours, filtered and concentrated in vacuo. Purification by flash chromatography on silica gel using a 220 g column and eluting with 30 to 100% EtOAc/hexanes provided the desired product as a white solid.

Workup

  1. temperatureThe reaction mixture was heated to 70° C. for 22 hours
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customPurification by flash chromatography on silica gel using a 220 g column
  5. washeluting with 30 to 100% EtOAc/hexanes

Sources & evidence

ORD record
ord-3958a753b1444e6cb812019c18ad4010
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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