Hydrochloric Acid → (3R,4S)-3-acetamido-N-tert-butyl-4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl]pyrrolidine-3-carboxamide hydrochloride

HRID 590743

반응식

HRID 590743 반응식
[C:1]([NH:4][C@:5]1([C:29](=[O:35])[NH:30][C:31]([CH3:34])([CH3:33])[CH3:32])[C@@H:9]([CH2:10][CH2:11][CH2:12][B:13]2[O:17][C:16]([CH3:19])([CH3:18])[C:15]([CH3:21])([CH3:20])[O:14]2)[CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6]1)(=[O:3])[CH3:2].[ClH:36].O1CCOCC1>C1COCC1.C(OCC)C>[ClH:36].[C:1]([NH:4][C@:5]1([C:29]([NH:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:35])[C@@H:9]([CH2:10][CH2:11][CH2:12][B:13]2[O:17][C:16]([CH3:18])([CH3:19])[C:15]([CH3:20])([CH3:21])[O:14]2)[CH2:8][NH:7][CH2:6]1)(=[O:3])[CH3:2]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67517991(3R,4S)-tert-butyl 3-acetamido-3-(tert-butylcarbamoyl)-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)pyrrolidine-1-carboxylate

생성물 1

HCID 67517412(3R,4S)-3-acetamido-N-tert-butyl-4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl]pyrrolidine-3-carboxamide hydrochloride수율 97%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

While under nitrogen, a stirred solution of tert-butyl (3R,4S)-3-acetamido-3-(tert-butylcarbamoyl)-4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl]pyrrolidine-1-carboxylate (400 mg, 0.807 mmol) in anhydrous THF (5 mL) was treated with 4 M HCl in 1,4-dioxane (3.03 mL, 12.1 mmol). After 2.5 h, the mixture was diluted with diethyl ether (15 mL) and filtered, washed with additional ether and concentrated to give (3R,4S)-3-acetamido-N-tert-butyl-4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl]pyrrolidine-3-carboxamide hydrochloride (340 mg, 97%) as a white solid. 1H NMR (D2O, 400 MHz) δ 4.11 (d, J=12 Hz, 1 H), 3.58 (dd, J=11.5, 7.7 Hz, 1 H), 3.19 (d, J=12 Hz, 1 H), 3.01 (t, J=11.5, 1 H), 2.42 (m, 1 H), 1.92 (s, 3 H), 1.52 (m, 1 H), 1.30 (m, 2 H), 1.19 (s, 9 H), 1.16 (s, 12 H), 1.08 (m, 1 H), 0.75 (m, 2 H). LC-MS gives ESI+ MS found for C20H38BN3O4 m/z 396.1 (M+H).

후처리

  1. filtrationfiltered
  2. washwashed with additional ether
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7b2ebfba871f4bbc935b0634bb5169f4
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233985B2

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