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p-Toluenesulfonic acid monohydrate → Trifluoroacetic acid

HRID 2357068
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HRID 2357068 반응식
CC1(C)[N:6](C(OC(C)(C)C)=O)[C@:5]([CH3:39])([C:14]([NH:16][NH:17][C:18](=O)[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[C:21]([C:34]([F:37])([F:36])[F:35])[CH:20]=2)=O)[CH2:4][O:3]1.[OH2:41].C1(C)C=CC([S:48](O)(=O)=[O:49])=CC=1>CO>[NH2:6][C@@:5]([C:14]1[S:48][C:18]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[C:21]([C:34]([F:37])([F:36])[F:35])[CH:20]=2)=[N:17][N:16]=1)([CH3:39])[CH2:4][OH:3].[C:21]([OH:49])([C:34]([F:37])([F:36])[F:35])=[O:41]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 53349361HCID 53349361, 화합물

생성물 2

HCID 6422Trifluoroacetic acid수율 233.9%HCID 250604211,3,4-Thiadiazole-2-ethanol, beta-amino-beta-methyl-5-[4-(octyloxy)-3-(trifluoromethyl)phenyl]-, (betaS)-

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of (S)-tert-butyl 2,2,4-trimethyl-4-(2-(4-(octyloxy)-3-(trifluoromethyl)-benzoyl)hydrazinecarbonyl)oxazolidine-3-carboxylate (14a) (156 mg, 0.27 mmol) in methanol (5 mL) was treated with p-toluenesulfonic acid monohydrate (259 mg, 1.36 mmol) at 70° C. for 2 hours. The reaction mixture was then cooled to room temperature and purified by prep HPLC on a C8(2) column ((Luna, 5μ, 100×21.10 mm) with acetonitrile-H2O (0.1% TFA) as mobile phase and gradient 30-98% in 20 min. The title compound was obtained as the bis-TFA salt (36 mg, 20%). MS (ESI): 432.00 (MH+); 1H NMR (400 MHz, DMSO-d6) δ 8.21 (dd, 1H, J=2.0 Hz, J=8.8 Hz), 8.15 (d, 1H, J=2.0 Hz), 8.09 (br s, 2H), 7.45 (d, 1H, J=8.8 Hz), 5.96 (t, 1H, J=4.8 Hz), 4.21 (t, 2H, J=6.4 Hz), 3.81 (dd, 1H, J=11.2 Hz, J=5.2 Hz), 3.73 (dd, 1H, J=11.2 Hz, J=5.2 Hz), 1.76 (m, 2H), 1.66 (s, 3H), 1.44 (m, 2H), 1.28 (m, 8H), 0.86 (t, 3H, J=6.8 Hz).

후처리

  1. custompurified by prep HPLC on a C8(2) column ((Luna, 5μ, 100×21.10 mm) with acetonitrile-H2O (0.1% TFA) as mobile phase and gradient 30-98% in 20 min

출처 및 근거

ORD 기록
ord-3f044eacf65942609a2777fd5a8148ba
출처 데이터셋
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07759370B2

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