Acetone → HCID 58573620, compound

HRID 932252Notes

Reaction equation

HRID 932252 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-ce414b3f88e840e2b25c87c82e9cc787
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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