Lithium Hydroxide → HCID 118093004, compound

HRID 708811Notes

Reaction equation

HRID 708811 reaction equation
[C:1]([O:5][C:6]([N:8]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C:9]1[C:18]2[C:13](=[CH:14][C:15]([NH:19][C@H:20]3[C:37](=[O:38])[N:36]([CH3:39])[CH2:35][C:34]4[CH:40]=[C:30]([CH:31]=[CH:32][C:33]=4[C:41]([O:43]C)=[O:42])[NH:29][C:28](=[O:45])[O:27][CH2:26][C@H:25]([CH3:46])[C:24]4[CH:47]=[CH:48][C:21]3=[CH:22][C:23]=4[CH3:49])=[CH:16][CH:17]=2)[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>C1COCC1>[C:53]([O:52][C:50]([N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[C:9]1[C:18]2[C:13](=[CH:14][C:15]([NH:19][C@H:20]3[C:37](=[O:38])[N:36]([CH3:39])[CH2:35][C:34]4[CH:40]=[C:30]([CH:31]=[CH:32][C:33]=4[C:41]([OH:43])=[O:42])[NH:29][C:28](=[O:45])[O:27][CH2:26][C@H:25]([CH3:46])[C:24]4[CH:47]=[CH:48][C:21]3=[CH:22][C:23]=4[CH3:49])=[CH:16][CH:17]=2)[CH:12]=[CH:11][N:10]=1)=[O:51])([CH3:56])([CH3:54])[CH3:55]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 118098682HCID 118098682, compound

Product 1

HCID 118093004HCID 118093004, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1C (25 mg, 0.033 mmol) in THF (1 mL) was added 1.0 N LiOH (0.5 mL) and the reaction mixture was stirred overnight. It was quenched with NH4Cl, extracted with EtOAC, washed with brine and concentrated. The crude was purified by prep HPLC (Axia Luna 5 u C18 30×100 mm) to give 1D (14 mg, 57% yield): MS (ESI) m/z: =754.3 [M+H]+.

Workup

  1. customIt was quenched with NH4Cl
  2. extractionextracted with EtOAC
  3. washwashed with brine
  4. concentrationconcentrated
  5. customThe crude was purified by prep HPLC (Axia Luna 5 u C18 30×100 mm)

Sources & evidence

ORD record
ord-0325d33e55164965b5f9207288a3ea67
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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