Water → HCID 11591529, compound

HRID 869341Notes

Reaction equation

HRID 869341 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:36])[N:6]2[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][S:21]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([O:34]C)=[O:33])=[CH:26][CH:25]=1)(=[O:23])=[O:22].[OH-].[Li+].O1CCCC1.O>C(O)(=O)C>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:36])[N:6]2[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][S:21]([C:24]1[CH:25]=[CH:26][C:27]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[CH:28][CH:29]=1)(=[O:22])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 11519234HCID 11519234, compound

Product 1

HCID 11591529HCID 11591529, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The compound obtained in Example 2-11 (100 mg) and lithium hydroxide (17 mg) were added to tetrahydrofuran (4 ml) and water (2 ml) and the mixture was stirred at room temperature for 16 hours. To the reaction solution was added acetic acid (2 ml) and the mixture was concentrated under reduced pressure. The residue was purified by RPHPLC and appropriate fractions were concentrated under reduced pressure to give the titled compound as a white solid. Yield: 40 mg (41%); mp 210-211° C., MS APCI+ve 507 (M+H).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customThe residue was purified by RPHPLC and appropriate fractions
  3. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-979e78fbd7ce4467b5057a319b6f71f4
Source dataset
uspto-grants-2015_03
Patent number
US08969362B2

Reaction notes

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