Sodium Hydroxide → HCID 70913602, compound

HRID 1844723Notes

Reaction equation

HRID 1844723 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:19]2[N:23]([CH2:24][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[C:22]([CH3:31])=[C:21]([S:32]([NH:35][CH2:36][C:37]([CH3:43])([CH3:42])[C:38]([O:40]C)=[O:39])(=[O:34])=[O:33])[CH:20]=2)[CH:8]=[CH:9][C:10]=1[S:11](=[O:18])(=[O:17])[NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([C:5]1[CH:6]=[C:7]([C:19]2[N:23]([CH2:24][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[C:22]([CH3:31])=[C:21]([S:32]([NH:35][CH2:36][C:37]([CH3:43])([CH3:42])[C:38]([OH:40])=[O:39])(=[O:34])=[O:33])[CH:20]=2)[CH:8]=[CH:9][C:10]=1[S:11](=[O:18])(=[O:17])[NH:12][C:13]([CH3:15])([CH3:16])[CH3:14])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86719136HCID 86719136, compound

Product 1

HCID 70913602HCID 70913602, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ester 10 (60 mg, 0.09 mmol) in MeOH (5 mL) was added 6N NaOH (1 mL). The mixture was stirred at rt overnight, the solvent was removed and the residue was adjusted ph<2 with 4N HCl, then extracted with EA (3×) and the combined organic layers were washed with brine and dried over Na2SO4, evaporated and purified by prep-HPLC to give acid 11 (38 mg, 65%) as white solid. 1H-NMR (400 MHz, DMSO-d6) δ: 12.29 (s, 1H), 8.15 (d, J=8.4 Hz, 1H), 7.81 (s, 1H), 7.53 (s, 1H), 7.47 (d, J=8.4 Hz, 1H), 7.14 (t, J=6.8 Hz, 1H), 6.47 (s, 1H), 3.87 (d, J=6.8 Hz, 2H), 2.83 (d, J=7.2 Hz, 2H), 2.45 (s, 3H), 1.55 (s, 9H), 1.44 (d, 3H), 1.19-1.16 (m, 12H), 1.05 (s, 6H), 0.89-0.84 (m, 3H), 0.66-0.57 (m, 2H). MS Calcd.: 623.3; MS Found: 624.2 (M+1).

Workup

  1. customthe solvent was removed
  2. extractionextracted with EA (3×)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-d5291b6a03864cbdb167a622fb3d815c
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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