Ammonia → HCID 16748202, compound

HRID 1350221Notes

Reaction equation

HRID 1350221 reaction equation
[NH2:1][CH2:2][C:3]1[N:7]=[C:6]([C@H:8]([CH2:17][CH2:18][CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[O:5][N:4]=1.C1C(=O)[N:30](OC(ON2C(=O)CCC2=O)=O)[C:28](=[O:29])C1.N>CC#N>[NH2:30][C:28]([NH:1][CH2:2][C:3]1[N:7]=[C:6]([C@H:8]([CH2:17][CH2:18][CH2:19][CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[CH2:9][C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11])[O:5][N:4]=1)=[O:29]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 676246Di(succinimido) carbonateHCID 16747946tert-butyl(3R)-3-[3-(aminomethyl)-1,2,4-oxadiazol-5-yl]-6-cyclohexylhexanoate

Product 1

HCID 16748202HCID 16748202, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of tert-butyl(3R)-3-[3-(aminomethyl)-1,2,4-oxadiazol-5-yl]-6-cyclohexylhexanoate (preparation 18) (310 mg, 0.88 mmol) in MeCN (10 ml) was treated with N,N-disuccinimidyl carbonate (271 mg, 1.06 mmol) and stirred at room temperature, under a nitrogen atmosphere for 4.5 hours. NH3 (0.5M in dioxan) was added forming a white precipitate. The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was filtered and the solvent removed under reduced pressure. The residue was purified on a silica column eluting with a solvent gradient of DCM:MeOH (100:0) gradually changing to (95:5) to afford the title compound as a colourless oil (253 mg, 73%).

Workup

  1. customforming a white precipitate
  2. stirringThe reaction mixture was stirred at room temperature for 18 hours
  3. filtrationThe reaction mixture was filtered
  4. customthe solvent removed under reduced pressure
  5. customThe residue was purified on a silica column
  6. washeluting with a solvent gradient of DCM:MeOH (100:0)

Sources & evidence

ORD record
ord-2584f46b06254dba96f192377f1d2e2f
Source dataset
uspto-grants-2007_05
Patent number
US07214694B2

Reaction notes

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