Trifluoroacetic acid → HCID 58619083, 화합물

HRID 1795179노트

반응식

HRID 1795179 반응식
[N:1]1([C:7]2([CH2:13][OH:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:15]([O:19][C:20]([NH:22][C@H:23]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:24](O)=[O:25])=[O:21])([CH3:18])([CH3:17])[CH3:16].ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C.FC(F)(F)C(O)=O>CN(C)C=O>[C:15]([O:19][C:20](=[O:21])[NH:22][C@H:23]([CH2:27][C:28]1[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=1)[C:24]([N:10]1[CH2:11][CH2:12][C:7]([CH2:13][OH:14])([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:8][CH2:9]1)=[O:25])([CH3:18])([CH3:16])[CH3:17]

참가 물질

8

반응물 6

HCID 6422Trifluoroacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 7018791N-Boc-4-chloro-D-phenylalanineHCID 22185336HCID 22185336, 화합물

생성물 1

HCID 58619083HCID 58619083, 화합물수율 43%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

To a round bottom flask equipped with a stirring bar is charged [1,4′]bipiperidinyl-4′-yl-methanol, 22, (2.2 g, 11.1 mmol, 1.0 eq.) 2-(R)-tert-butoxycarbonylamino-3-(4-chlorophenyl)-propionic acid (3.648 g, 12.2 mmol), 1-hydroxybenzotriazole (2.552 g, 18.9 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (3.71 g, 18.9 mmol) in anhydrous N,N-dimethylformamide (80 mL). The mixture is cooled to 0° C. and N,N-diisopropyl-ethylamine (4.1 mL, 37.7 mmol) is added. The ice bath is removed and the reaction mixture allowed to stir overnight. The mixture is concentrated under reduced pressure and purified by preparative HPLC to afford 2.83 g (43% yield) of the desired compound as the trifluoroacetic acid salt. 1H NMR (CD3OD, 300 MHz) δ 0.85–2.13 (m, 19H), 2.65–3.82 (m, 8H), 3.90–4.10 (m, 3H), 4.48 (m, 1H), 4.76 (m, 1H), 7.22–7.48 (m, 4H). MS (ESI) m/z 480 (M+H+).

후처리

  1. customTo a round bottom flask equipped with a stirring bar
  2. customThe ice bath is removed
  3. concentrationThe mixture is concentrated under reduced pressure
  4. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-059dc44b6d694ad197435a022983b47a
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07026335B2

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