Triphenylphosphine → HCID 118307766, 화합물

HRID 718455노트

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HRID 718455 반응식
[C:1]([O:5][C@@H:6]([C:12]1[C:13]([CH3:34])=[N:14][C:15]([CH3:33])=[C:16]([C:26]2[CH:31]=[CH:30][C:29](O)=[CH:28][CH:27]=2)[C:17]=1[N:18]1[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[CH2:20][CH2:19]1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH3:35][C:36]1[S:40][C:39]([CH2:41][CH2:42][OH:43])=[CH:38][CH:37]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH-].[Na+]>C1COCC1.CO>[C:1]([O:5][C@@H:6]([C:12]1[C:13]([CH3:34])=[N:14][C:15]([CH3:33])=[C:16]([C:26]2[CH:27]=[CH:28][C:29]([O:43][CH2:42][CH2:41][C:39]3[S:40][C:36]([CH3:35])=[CH:37][CH:38]=3)=[CH:30][CH:31]=2)[C:17]=1[N:18]1[CH2:19][CH2:20][C:21]([CH3:25])([CH3:24])[CH2:22][CH2:23]1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

참가 물질

8

반응물 5

HCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 5363146Diisopropyl azodicarboxylateHCID 1328928919498-70-5HCID 118314205(S)-ethyl 2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-5-(4-hydroxyphenyl)-2,6-dimethylpyridin-3-yl)acetate

생성물 1

HCID 118307766HCID 118307766, 화합물수율 21.57%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of (S)-ethyl 2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-5-(4-hydroxyphenyl)-2,6-dimethylpyridin-3-yl)acetate (50 mg, 0.107 mmol), 2-(5-methylthiophen-2-yl)ethanol (76 mg, 0.533 mmol) and Ph3P (139 mg, 0.533 mmol) in THF (2 mL) was added DIAD (0.104 mL, 0.533 mmol) at rt. After 18 h, mixture was filtered to remove polymer, concentrated and treated with 1N NaOH (0.854 mL, 0.854 mmol) in MeOH (1 mL) at 75° C. for 16 h. Mixture was then cooled and purified by prep-HPLC to afford (S)-2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethyl-5-(4-(2-(5-methylthiophen-2-yl)ethoxy)phenyl)pyridin-3-yl)acetic acid (13 mg, 0.023 mmol, 21.57% yield). 1H NMR (500 MHz, DMSO-d6) δ 7.20 (d, J=8.8 Hz, 1H), 7.10-6.91 (m, 4H), 6.73 (d, J=3.3 Hz, 1H), 6.63 (br. s., 1H), 5.82 (s, 1H), 4.29-4.07 (m, 3H), 3.26 (br. s., 1H), 3.17 (t, J=6.1 Hz, 1H), 2.43 (s, 3H), 2.38 (s, 3H), 2.15 (br. s., 1H), 2.05 (s, 3H), 1.28 (br. s., 2H), 1.17 (d, J=16.5 Hz, 1H), 1.11 (s, 9H), 1.07-0.94 (m, 2H), 0.83 (br. s., 3H), 0.60 (br. s., 3H). LCMS (M+H)=565.3.

후처리

  1. filtrationmixture was filtered
  2. customto remove polymer
  3. concentrationconcentrated
  4. temperatureMixture was then cooled
  5. custompurified by prep-HPLC

출처 및 근거

ORD 기록
ord-1442174ba8594f86a52b32e815116820
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193720B2

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