Sodium Hydroxide → HCID 178454261, compound

HRID 526820Notes

Reaction equation

HRID 526820 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:60][C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62])[C:24](=[O:59])[NH:25][CH2:26][CH2:27][CH2:28][CH2:29][C@H:30]([NH:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[C:31](=[O:50])[NH:32][CH2:33][CH2:34][CH2:35][CH2:36][C@H:37]([NH:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[C:38]([O:40]C)=[O:39])=[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:60][C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62])[C:24](=[O:59])[NH:25][CH2:26][CH2:27][CH2:28][CH2:29][C@H:30]([NH:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[C:31](=[O:50])[NH:32][CH2:33][CH2:34][CH2:35][CH2:36][C@H:37]([NH:42][C:43]([O:45][C:46]([CH3:47])([CH3:48])[CH3:49])=[O:44])[C:38]([OH:40])=[O:39])=[N:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:17])([CH3:14])([CH3:15])[CH3:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178501439HCID 178501439, compound

Product 1

HCID 178454261HCID 178454261, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of methyl ester 48 (1.40 g, 1.32 mmol) in MeOH/THF/H2O (45 mL/45 mL/15 mL) was charged with NaOH (265 mg, 6.61 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 aqueous 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 49 (1.20 g, 87%) as a white solid, which was used directly in the next step: 1H NMR (400 MHz, CD3OD) δ 4.06-3.89 (m, 3H), 3.35 (t, J=7.6 Hz, 2H), 3.25-3.11 (m, 4H), 1.86-1.66 (m, 3H), 1.64-1.55 (m, 5H), 1.54-1.30 (m, 10H), 1.52 (s, 9H), 1.46 (s, 9H), 1.43 (s, 27H).

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) The combined organic extracts
  6. dry with materialwere dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a830764e27e2405bb9dd8944c61be924
Source dataset
uspto-grants-2016_05
Patent number
US09346753B2

Reaction notes

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