N-Phthaloylglycine → HCID 67713329, compound

HRID 1378251Notes

Reaction equation

HRID 1378251 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([N:9]([CH2:12][C:13]([OH:15])=O)[C:10](=[O:11])[C:4]2=[CH:3][CH:2]=1)=[O:8].C(N1C=CN=C1)(N1C=CN=C1)=O.[O:28]=[C:29]1[N:35]2[CH2:36][CH2:37][CH2:38][C@H:34]2[C:33]2=[C:39]([C:42]([NH:44][NH2:45])=[O:43])[N:40]=[CH:41][N:32]2[C:31]2[CH:46]=[CH:47][S:48][C:30]1=2>CN(C)C=O>[O:11]=[C:10]1[C:4]2[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=2)[C:7](=[O:8])[N:9]1[CH2:12][C:13]([NH:45][NH:44][C:42]([C:39]1[N:40]=[CH:41][N:32]2[C:31]3[CH:46]=[CH:47][S:48][C:30]=3[C:29](=[O:28])[N:35]3[CH2:36][CH2:37][CH2:38][C@H:34]3[C:33]=12)=[O:43])=[O:15]

Participants

5

Reactant 3

HCID 20825N-PhthaloylglycineHCID 682631,1'-CarbonyldiimidazoleHCID 67713483HCID 67713483, compound

Product 1

HCID 67713329HCID 67713329, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.0 g (4.9 mmol) of N-phthaloylglycine in 8 ml of dimethylformamide was treated at room temperature with 0.83 g is (5.11 mmol) of 1,1'-carbonyldiimidazole and the mixture was subsequently heated to 50°. After 30 minutes the mixture was cooled to room temperature, 1.5 g (5 mmol) of (S)-10,11,12,12a-tetrahydro-8-oxo-8H-imidazo[5,1-c]pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine-1-carboxylic acid hydrazide were added thereto and the mixture was stirred at room temperature for 12 hours. The suspension obtained was filtered and the colourless powder obtained was washed with ethanol and diethyl ether. There were obtained 2.2 g (100%) of (S)-N'-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-ylacetyl)-8-oxo-10,11,12,12a-tetrahydro-8H-imidazo[5,1-c]pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine-1-carboxylic acid hydrazide of m.p. >260°.

Workup

  1. temperaturethe mixture was subsequently heated to 50°
  2. customThe suspension obtained
  3. filtrationwas filtered
  4. customthe colourless powder obtained
  5. washwas washed with ethanol and diethyl ether

Sources & evidence

ORD record
ord-4ff756c2aeba4ec8880d7adb07891b69
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

Loading…