Sodium Hydroxide → HCID 178454263, compound

HRID 526816Notes

Reaction equation

HRID 526816 reaction equation
[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]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178501438HCID 178501438, compound

Product 1

HCID 178454263HCID 178454263, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of methyl ester 20 (6.00 g, 8.21 mmol) in MeOH/THF/H2O (100 mL/100 mL/50 mL) was charged with NaOH (1.64 g, 41.1 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 (150 mL) and water (100 mL). The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (2×150 mL). The combined organic extracts were dried over Na2SO4 and concentrated to afford compound 21 (5.50 g, 94%) as a white solid, which was used directly in the next step: 1H NMR (400 MHz, CD3OD) δ 4.06-4.00 (m, 1H), 4.00-3.93 (m, 1H), 3.35 (t, J=7.3 Hz, 2H), 3.26-3.07 (m, 2H), 1.85-1.56 (m, 6H), 1.53-1.32 (m, 6H), 1.52 (s, 9H), 1.46 (s, 9H), 1.438 (s, 9H), 1.435 (s, 9H).

Workup

  1. customAfter completion of the reaction
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customThe suspension was partitioned between CH2Cl2 (150 mL) and water (100 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with CH2Cl2 (2×150 mL)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5a4609a040dc415c8239160126bde207
Source dataset
uspto-grants-2016_05
Patent number
US09346753B2

Reaction notes

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