2-Phenylisobutyric acid → Ammonium Acetate

HRID 218221

반응식

HRID 218221 반응식
Cl.[CH:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH:3]1[NH2:12])[CH2:9]2.[C:13]1([C:19]([CH3:24])([CH3:23])[C:20]([OH:22])=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CN(C)C(=O)C>[C:20]([O-:22])(=[O:21])[CH3:19].[NH4+:12].[CH:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH:3]1[NH:12][C:20](=[O:21])[C:19]([CH3:23])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:24])[CH2:9]2

참가 물질

7

반응물 4

HCID 132222-Phenylisobutyric acidHCID 253312-Aminoadamantane hydrochlorideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

생성물 2

HCID 517165Ammonium AcetateHCID 10266665HCID 10266665, 화합물

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

A solution of 2-adamantanamine hydrochloride (38 mg, 0.20 mmol), 2-phenylisobutyric acid (30 mg, 0.19 mmol), and O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) (65 mg, 0.20 mmol) in N,N-dimethylacetamide (DMA) (2 mL) and DIEA (80 μL, 0.46 mmol) was stirred for 16 hours at 23° C. The reaction mixture was analyzed by LC/MS and determined to be near completion. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in DMSO/MeOH (1:1, 1.5 mL) and purified by preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 um particle size) using a gradient of 10% to 100% acetonitrile:aqueous ammonium acetate (10 mM) over 8 minutes (10 minute run time) at a flow rate of 40 mL/minute on reverse phase HPLC to afford the title compound upon concentration under reduced pressure. 1H NMR (300 MHz, DMSO-d6) δ 7.35 (m, 4H), 7.24 (m, 1H), 6.16 (d, J=6.9 Hz, 1H), 3.78 (m, 1H), 1.74 (m, 7H), 1.64 (m, 3H), 1.55 (m, 2H), 1.48 (s, 6H), 1.41 (m, 2H); MS (DCI+) m/z 298 (M+H)+.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in DMSO/MeOH (1:1, 1.5 mL)
  3. custompurified by preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 um particle size)

출처 및 근거

ORD 기록
ord-9666be7dfffa40e7b24262f61b1b56a7
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198331B2

연결된 노트

불러오는 중…