Lithium Hydroxide → HCID 86635877, compound

HRID 1698446Notes

Reaction equation

HRID 1698446 reaction equation
[C:1]([NH:11][C@@H:12]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C@H:13]([OH:31])[CH2:14][N:15]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:16](=[O:23])[C:17](=[N+:21]=[N-:22])C(=O)C)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[Li+].[OH-]>C1COCC1.O.O.ClCCl>[C:1]([NH:11][C@@H:12]([CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C@H:13]([OH:31])[CH2:14][N:15]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:16](=[O:23])[CH:17]=[N+:21]=[N-:22])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 86635875HCID 86635875, compound

Product 1

HCID 86635877HCID 86635877, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

The diazo ketamide (XII) (0.020 g, 0.038 mmol) was dissolved in 0.5 ml of 1:1 THF/H2O and to this LiOH (5 mg, 0.19 mmol) dissolved in 0.2 ml of water was added. The reaction mixture was stirred for 5 hrs and diluted with 2 ml of dichloromethane. The organic layer was separated, dried (Na2SO4), and concentrated. The product (XIII) was then isolated by passing through a plug of silica as an oil. 0.015 g. (81% yield). 1H NMR (500 MHz, CDCl3) δ 7.13-7.49 (m, 15H), 5.02-5.37 (m, 3H), 4.46-4.87 (m, 2H), 3.75-4.04 (m, 2H), 3.28-3.47 (m, 1H), 2.75-2.94 (m, 2H). 13CNMR (125 MHz, CDCl3) 163.4, 155.85, 140.91, 140.36, 139.22, 129.14, 128.68, 128.26, 128.17, 128.10, 127.72, 127.41, 127.64, 126.75, 78.33, 60.18, 52.04, 50.15, 46.89, 44.7, 36.43.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1b38950cc55d486da6857e9b6b9d07af
Source dataset
uspto-grants-2012_04
Patent number
US08163953B2

Reaction notes

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