Sodium Hydroxide → HCID 178454262、化合物

HRID 526814ノート

反応式

HRID 526814 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C@@H:23]([NH:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[C:24](=[O:43])[NH:25][CH2:26][CH2:27][CH2:28][CH2:29][C@@H:30]([NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:31]([O:33]C)=[O:32])=[N:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.C1COCC1.O>[C:13]([O:12][C:11]([NH:10][C:9]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C@@H:23]([NH:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[C:24](=[O:43])[NH:25][CH2:26][CH2:27][CH2:28][CH2:29][C@@H:30]([NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:31]([OH:33])=[O:32])=[N:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:17])([CH3:14])([CH3:15])[CH3:16]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 178501437HCID 178501437、化合物

生成物 1

HCID 178454262HCID 178454262、化合物収率 86%

試薬・触媒・溶媒 1

HCID 21892291Methanol tetrahydrofuran water溶媒

実験手順

A solution of methyl ester 15 (2.15 g, 2.94 mmol) in MeOH/THF/H2O (30 mL/30 mL/15 mL) was charged with NaOH (589 mg, 14.7 mmol) and the reaction mixture was stirred at room temperature for 1 h. After completion of the reaction, the mixture was concentrated under reduced pressure and the pH was adjusted to 5 with 1 N HCl. The suspension was partitioned between CH2Cl2 (50 mL) and water (50 mL). The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (2×50 mL). The combined organic extracts were dried over Na2SO4 and concentrated to afford compound 16 (1.80 g, 86%) as a white solid, which was used directly in the next step: 1H NMR (400 MHz, CD3OD) δ 4.07-4.00 (m, 1H), 4.00-3.91 (m, 1H), 3.35 (t, J=7.2 Hz, 2H), 3.25-3.10 (m, 2H), 1.89-1.23 (m, 12H), 1.52 (s, 9H), 1.46 (s, 9H), 1.438 (s, 9H), 1.436 (s, 9H).

後処理

  1. customAfter completion of the reaction
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customThe suspension was partitioned between CH2Cl2 (50 mL) and water (50 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with CH2Cl2 (2×50 mL)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-21f80980a30a439c97d71b6eea96326e
出典データセット
uspto-grants-2016_05
特許番号
US09346753B2

反応ノート

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