Water → HCID 58044091, compound

HRID 1918993Notes

Reaction equation

HRID 1918993 reaction equation
C([O:4][CH2:5][C:6]1[C:11]([N:12]2[CH2:24][CH2:23][N:15]3[C:16]4[CH2:17][CH2:18][CH2:19][CH2:20][C:21]=4[CH:22]=[C:14]3[C:13]2=[O:25])=[CH:10][CH:9]=[CH:8][C:7]=1[C:26]1[CH:31]=[C:30]([NH:32][C:33]2[CH:37]=[CH:36][N:35]([CH2:38][CH2:39][N:40]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH3:41])[N:34]=2)[C:29](=[O:49])[N:28]([CH3:50])[CH:27]=1)(=O)C.O.[Li+].[OH-]>CC(O)C.O1CCCC1>[OH:4][CH2:5][C:6]1[C:11]([N:12]2[CH2:24][CH2:23][N:15]3[C:16]4[CH2:17][CH2:18][CH2:19][CH2:20][C:21]=4[CH:22]=[C:14]3[C:13]2=[O:25])=[CH:10][CH:9]=[CH:8][C:7]=1[C:26]1[CH:31]=[C:30]([NH:32][C:33]2[CH:37]=[CH:36][N:35]([CH2:38][CH2:39][N:40]([CH3:41])[C:42](=[O:43])[O:44][C:45]([CH3:46])([CH3:47])[CH3:48])[N:34]=2)[C:29](=[O:49])[N:28]([CH3:50])[CH:27]=1

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 67016491HCID 67016491, compound

Product 1

HCID 58044091HCID 58044091, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of 206g (750 mg, 1.1 mmol) in propan-2-ol (15 mL), tetrahydrofuran (15 mL), and water (5 mL) was added LiOH (2.6 g, 110 mmol). The mixture was stirred at 30° C. for 2 h. It was then evaporated and the residue was purified by reverse phase Combi-flash eluting with 0.3% NH4HCO3 in 1:3 water/CH3CN to give 206h as a brown solid (500 mg, 71%). MS: (M+H)+ 642

Workup

  1. customIt was then evaporated
  2. customthe residue was purified by reverse phase Combi-flash
  3. washeluting with 0.3% NH4HCO3 in 1:3 water/CH3CN

Sources & evidence

ORD record
ord-443a863b6072494681fc45232288333f
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

Loading…