Water → HCID 178483847, compound

HRID 1486225Notes

Reaction equation

HRID 1486225 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([CH2:15][C:16]([OH:18])=[O:17])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Na+].[Na+].C(Br)[C:26]1[CH:31]=CC=CC=1.O.[CH3:34][N:35](C=O)[CH3:36]>>[C:1]([O:5][C:6]([N:8]([CH2:26][CH2:31][N:35]([CH3:36])[CH3:34])[C@H:9]1[CH2:10][CH2:11][C@H:12]([CH2:15][C:16]([OH:18])=[O:17])[CH2:13][CH2:14]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 178453927HCID 178453927, compound

Product 1

HCID 178483847HCID 178483847, compound

Procedure

To 2-(trans-4-(tert-butoxycarbonylamino)cyclohexyl)acetic acid (1.47 g) in DMF (10 mL) was added Na2CO3 (0.907 g) and benzyl bromide (0.75 mL). The resultant reaction mixture was stirred at RT for overnight. Water was then added and extracted with EtOAc. The organic phase was dried and concentrated to afford the desired product as white solid (1.60 g). To this solid was added 4N HCl (10 mL) and the reaction mixture was stirred at RT for 1 hr. Diethyl ether was then added to the reaction mixture to precipitate out the benzyl 2-(trans-4-aminocyclohexyl)acetate HCl salt as white solid.

Workup

  1. customThe resultant reaction mixture
  2. extractionextracted with EtOAc
  3. customThe organic phase was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9a8232307ef145b38535fd2a41410a5f
Source dataset
uspto-grants-2016_08
Patent number
US09422314B2

Reaction notes

Loading…