Tetrahydrofuran → HCID 21201830, compound

HRID 1979450Notes

Reaction equation

HRID 1979450 reaction equation
[C:1]1([C:6]([CH2:8][N:9]2[C:15]3[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:14]=3[N:13]([C:21](=[O:27])[C:22]3[S:26][CH:25]=[CH:24][CH:23]=3)[CH2:12][CH:11]([NH:28][C:29]([NH:31][C:32]3[CH:37]=[CH:36][C:35](C(OCC)=O)=[CH:34][CH:33]=3)=[O:30])[C:10]2=[O:43])=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1.[OH2:44].[OH-].[Li+].[O:47]1[CH2:51]CCC1>>[C:1]1([C:6]([CH2:8][N:9]2[C:15]3[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:14]=3[N:13]([C:21](=[O:27])[C:22]3[S:26][CH:25]=[CH:24][CH:23]=3)[CH2:12][CH:11]([NH:28][C:29](=[O:30])[NH:31][C:32]3[CH:37]=[C:36]([CH:35]=[CH:34][CH:33]=3)[C:51]([OH:47])=[O:44])[C:10]2=[O:43])=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 21201727HCID 21201727, compound

Product 1

HCID 21201830HCID 21201830, compound

Conditions

Temperature
45 °C

Procedure

1-[1-(2-Thenoylmethyl)-2-oxo-5-(2-thenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(4-ethoxycarbonylphenyl)urea (1.3 g) was suspended in tetrahydrofuran (30 ml), aqueous lithium hydroxide monohydrate (0.44 g) solution (15 ml) was added, the mixture was stirred at 40-50° C. for 6 hours. The solvent was concentrated under reduced pressure, 1N hydrochloric acid and chloroform were added to the residue, crystals so precipitated were collected by filtration, washed with a mixed solvent(chloroform:methanol=10:1), and filtrated by means of suction, to thereby obtain 102 mg of the title compound.

Workup

  1. concentrationThe solvent was concentrated under reduced pressure, 1N hydrochloric acid and chloroform
  2. additionwere added to the residue, crystals
  3. customso precipitated
  4. filtrationwere collected by filtration
  5. washwashed with a mixed solvent(chloroform:methanol=10:1)
  6. filtrationfiltrated by means of suction

Sources & evidence

ORD record
ord-d0816ab57f6a415db2d3b2d402bf7225
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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