Water → HCID 178483847, compound

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

Reactant 5

HCID 962Water

HCID 6228Dimethylformamide

HCID 7498Benzyl Bromide

HCID 10340Sodium Carbonate

HCID 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.