Triethylamine → HCID 86665067, 화합물

HRID 333312노트

반응식

HRID 333312 반응식
[CH2:1]([O:8][C:9](=[O:19])[CH2:10][C:11]1([C:16]([OH:18])=O)[CH2:15][CH2:14][CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][C@@H:21]([C:35]1[N:39]([CH2:40][CH2:41][C:42]#[N:43])[N:38]=[N:37][N:36]=1)[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:25][CH:24]=1.CCN=C=NCCCN(C)C.Cl.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[C:26]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:25]=[CH:24][C:23]([CH2:22][C@@H:21]([NH:20][C:16]([C:11]2([CH2:10][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15]2)=[O:18])[C:35]2[N:39]([CH2:40][CH2:41][C:42]#[N:43])[N:38]=[N:37][N:36]=2)=[CH:28][CH:27]=1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 596082261-(2-(Benzyloxy)-2-oxoethyl)cyclopentanecarboxylic acidHCID 68753516HCID 68753516, 화합물

생성물 1

HCID 86665067HCID 86665067, 화합물수율 44.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 1-(2-(benzyloxy)-2-oxoethyl)cyclopentanecarboxylic acid (49.4 mg, 0.188 mmol) and (R)-3-(5-(1-amino-2-(biphenyl-4-yl)ethyl)-1H-tetrazol-1-yl)propanenitrile (50 mg, 0.157 mmol) in DMF (1.5 mL) were added EDC.HCl (36 mg, 0.188 mmol), HOAt (26 mg, 0.188 mmol) and triethylamine (0.033 mL, 0.236 mmol). After being stirred for 2 hours, the reaction mixture was diluted with EtOAc. The mixture was washed with H2O2O and brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel flash column chromatography (eluent; EtOAc/heptane) to give (R)-benzyl 2-(1-(2-(biphenyl-4-yl)-1-(1-(2-cyanoethyl)-1H-tetrazol-5-yl)ethylcarbamoyl)cyclopentyl)acetate (39 mg). LCMS (condition A) δ 563 (M+1); retention time=1.85 min.

후처리

  1. washThe mixture was washed with H2O2O and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel flash column chromatography (eluent; EtOAc/heptane)

출처 및 근거

ORD 기록
ord-7894521324934f12a7a1d66cd91e2fc1
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877815B2

반응 노트

불러오는 중…