Water → HCID 57696171, compound

HRID 604246Notes

Reaction equation

HRID 604246 reaction equation
O.O.[OH-].[Li+].C([O:7][C:8](=[O:33])[CH2:9][NH:10][C:11](=[O:32])[CH2:12][NH:13][C:14](=[O:31])[C@H:15]([CH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)[NH:16][C:17]([C:19]1[O:20][CH:21]=[CH:22][CH:23]=1)=[O:18])C>O1CCCC1.O.C(O)C>[O:20]1[CH:21]=[CH:22][CH:23]=[C:19]1[C:17]([NH:16][C@H:15]([C:14]([NH:13][CH2:12][C:11]([NH:10][CH2:9][C:8]([OH:33])=[O:7])=[O:32])=[O:31])[CH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:18]

Participants

6

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 86630336HCID 86630336, compound

Product 1

HCID 57696171HCID 57696171, compoundYield 96.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 19096565Water ethanolSolvent2×

Procedure

Water (0.1 mL) and 2.7 mg of lithium hydroxide hydrate (0.0643 mmol) were added to a solution of 22.5 mg of 2-furoyl-β-cyclohexyl-L-alanyl-glycyl-glycine ethyl ester (0.0552 mmol) in tetrahydrofuran (0.2 mL). After stirring for 1 hour at room temperature, water-ethanol (1:10, 0.5 mL) and 48.1 mg of IRC-50 (about 0.48 mg equivalent) were added and the mixture was stirred for 0.5 hour. IRC-50 (0.3 mg) was swelled in water-ethanol (1:10), and filled in a glass tube, and the mixture was placed on the column, and then the column was eluted by water-ethanol (1:10, 7.5 mL). The eluate was concentrated under reduced pressure, whereby 20.3 mg of the title compound was obtained as a colorless oil.

Workup

  1. stirringthe mixture was stirred for 0.5 hour
  2. additionfilled in a glass tube
  3. washthe column was eluted by water-ethanol (1:10, 7.5 mL)
  4. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6386f48601c14315afcc7046d2716901
Source dataset
uspto-grants-2011_03
Patent number
US07910556B2

Reaction notes

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