Sodium Hydroxide → HCID 117901319, compound

HRID 526819Notes

Reaction equation

HRID 526819 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:22](=[O:57])[NH:23][CH2:24][CH2:25][CH2:26][CH2:27][C@H:28]([NH:49][C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C:29](=[O:48])[NH:30][CH2:31][CH2:32][CH2:33][CH2:34][C@H:35]([NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C:36]([O:38]C)=[O:37])[CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.C1COCC1.O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:22](=[O:57])[NH:23][CH2:24][CH2:25][CH2:26][CH2:27][C@H:28]([NH:49][C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C:29](=[O:48])[NH:30][CH2:31][CH2:32][CH2:33][CH2:34][C@H:35]([NH:40][C:41]([O:43][C:44]([CH3:46])([CH3:45])[CH3:47])=[O:42])[C:36]([OH:38])=[O:37])[CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 117901343HCID 117901343, compound

Product 1

HCID 117901319HCID 117901319, compoundYield 108.5%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of methyl ester 45 (2.00 g, 2.18 mmol) in MeOH/THF/H2O (60 mL/60 mL/20 mL) was charged with NaOH (436 mg, 10.9 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 of the solution was adjusted to 5 with 1 N HCl. The suspension was partitioned between CH2Cl2 (50 mL) and water (10 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 46 (1.90 g, 97%) as a white solid, which was used directly in the next step: 1H NMR (400 MHz, CD3OD) δ 4.08-4.00 (m, 1H), 3.98-3.89 (m, 2H), 3.27-3.10 (m, 4H), 3.02 (t, J=6.6 Hz, 2H), 1.86-1.65 (m, 4H), 1.64-1.24 (m, 14H), 1.43 (s, 18H), 1.42 (s, 18H).

Workup

  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 (10 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

Sources & evidence

ORD record
ord-5e789dd6af704d10bc0b621125ef6e95
Source dataset
uspto-grants-2016_05
Patent number
US09346753B2

Reaction notes

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