Hydrochloric Acid → HCID 66832956、化合物

HRID 579576

反応式

HRID 579576 の反応式
C([NH:4][C:5]([C@@H:26]1[CH2:30][CH2:29][N:28]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[CH2:27]1)([CH2:13][CH2:14][CH2:15][CH2:16][B:17]1[O:21]C(C)(C)C(C)(C)[O:18]1)[C:6](NC(C)(C)C)=[O:7])(=O)C.[ClH:39].[OH2:40]>>[ClH:39].[ClH:39].[NH2:4][C:5]([C@@H:26]1[CH2:30][CH2:29][N:28]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[CH2:27]1)([CH2:13][CH2:14][CH2:15][CH2:16][B:17]([OH:21])[OH:18])[C:6]([OH:7])=[O:40]

参加物

4

反応物 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 668334802-acetamido-N-tert-butyl-2-((R)-1-(4-fluorobenzyl)pyrrolidin-3-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanamide

生成物 1

HCID 66832956HCID 66832956、化合物

実験手順

An aqueous solution of 2-acetamido-N-tert-butyl-2-((R)-1-(4-fluorobenzyl)pyrrolidin-3-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanamide (0.280 g, 0.527 mmol) in 6M hydrogen chloride (10 mL, 60 mmol) was heated under reflux overnight. The reaction was cooled to room temperature, diluted with 20 mL of water, and washed with ethyl acetate (20 mL). The aqueous layer was purified by HPLC (3 injections) using a 5-20% acetonitrile in water. The fractions corresponding to the desired product were concentrated and lyophilized to give 2-amino-6-borono-2-((R)-1-(4-fluorobenzyl)pyrrolidin-3-yl)hexanoic acid dihydrochloride as white powder, which became oily upon exposure to air (hydroscopic). (0.003 g, 2%). 1H NMR (400 MHz, CDCl3, Mixture of diastereoisomers) δ 7.41 (dd, J1=8.1 Hz, J2=6.5 Hz, 2H), 7.12 (t, J=8.1 Hz, 2H), 4.35-4.25 (br, m, 2H), 3.77-3.09 (br. m, 3H), 2.99-2.60 (br. m, 1H), 2.39-1.57 (br. m, 4H), 1.34-1.18 (br. m, 2H), 1.15-1.03 (br. m, 1H), 0.70-0.61 (m, 2H),; ESI MS found for C17H26BFN2O4 m/z 335.3 (M+H-water)+; 351.4 (M−H)−; 333.4 (M−H-water)−.

後処理

  1. temperatureunder reflux overnight
  2. washwashed with ethyl acetate (20 mL)
  3. customThe aqueous layer was purified by HPLC (3 injections)
  4. concentrationThe fractions corresponding to the desired product were concentrated

出典と根拠

ORDレコード
ord-598292f35e264767a9ecce51abe58726
出典データセット
uspto-grants-2015_05
特許番号
US09040703B2

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