Methanol → HCID 68580570, compound

HRID 643827Notes

Reaction equation

HRID 643827 reaction equation
C([O:3][C:4]([C:6]12[CH2:24][CH:23]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:14](=[O:33])[N:13]1[CH:9]([CH2:10][CH:11]([O:34][C:35]3[C:44]4[C:39](=[CH:40][C:41]([O:45][CH3:46])=[CH:42][CH:43]=4)[N:38]=[C:37]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[CH:36]=3)[CH2:12]1)[C:8](=[O:53])[NH:7]2)=[O:5])C.O.CO.[OH-].[Li+]>O1CCCC1>[C:29]([O:28][C:26]([NH:25][N:15]1[C:14](=[O:33])[N:13]2[CH:9]([CH2:10][CH:11]([O:34][C:35]3[C:44]4[C:39](=[CH:40][C:41]([O:45][CH3:46])=[CH:42][CH:43]=4)[N:38]=[C:37]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[CH:36]=3)[CH2:12]2)[C:8](=[O:53])[NH:7][C:6]2([C:4]([OH:5])=[O:3])[CH:23]([CH2:24]2)[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:27])([CH3:32])([CH3:30])[CH3:31]

Participants

6

Reactant 4

HCID 887MethanolHCID 962Water2×HCID 3939Lithium HydroxideHCID 68578578HCID 68578578, compound

Product 1

HCID 68580570HCID 68580570, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 17 (39 mg, 0.054 mmol) was dissolved in tetrahydrofuran (3.5 ml), water (1.75 ml) and methanol (1.75 ml). Lithium hydroxide (430 μl, 1 M in water) was then added and the reaction was stirred at room temperature for 24 h. The volume was reduced to half and water (10 ml) was added. Acidification (pH=5) followed by extraction with chloroform gave the pure title compound (34 mg, 90%). MS (M+H+) 700.2

Workup

  1. additionwas added
  2. extractionAcidification (pH=5) followed by extraction with chloroform

Sources & evidence

ORD record
ord-36196cb738f4469e84a2cf855b95dc7f
Source dataset
uspto-grants-2010_04
Patent number
US07700552B2

Reaction notes

Loading…