Methanol → HCID 10155103, compound

HRID 1860686Notes

Reaction equation

HRID 1860686 reaction equation
C([O:3][C:4](=[O:28])[CH2:5][C:6]([CH3:27])([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:12][CH:11]=1)[CH:7]=[CH2:8])C.[OH-].[Na+].CO>O>[CH3:27][C:6]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:12][CH:11]=1)([CH:7]=[CH2:8])[CH2:5][C:4]([OH:28])=[O:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 12018743HCID 12018743, compound

Product 1

HCID 10155103HCID 10155103, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the product of STEP 7 (0.26 g), 1 N sodium hydroxide in water (2 ml), and methanol (4 ml) was stirred overnight. Solvent was removed. The crude product was purified on a reverse phase HPLC using acetonitrile/water (0.5% TFA) gradient to give colorless oil (0.150 g). Anal. MS (APCI): m/z=355 (MH+), 1H NMR (500 MHz, CD3OD): δ1.09 (3H, s), 2.16 (2H, m), 2.25 (2H, q), 2.70 (2H, s), 3.59 (2H, t), 4.08 (2H, t), 4.85 (1H, d), 4.98 (1H, d), 5.92 (1H, dd), 6.81 (2H, d), 6.84 (1H, t), 7.07 (3H, m), 7.79 (1H, d), 7.86 (1H. t). Calcd. for C21H26N2O3+1.1 TFA: C, 58.07; H, 5.69; N, 5.84, Found: C, 57.87; H, 5.77; N, 5.70.

Workup

  1. customSolvent was removed
  2. customThe crude product was purified on a reverse phase

Sources & evidence

ORD record
ord-90788a8f29814c62b7e51644e410f189
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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