N-Phthaloylglycine → HCID 67713642, compound

HRID 1378255Notes

Reaction equation

HRID 1378255 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][C@H:34]2[C:33]2=[C:38]([C:41]([NH:43][NH2:44])=[O:42])[N:39]=[CH:40][N:32]2[C:31]2[CH:45]=[CH:46][S:47][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:44][NH:43][C:41]([C:38]1[N:39]=[CH:40][N:32]2[C:31]3[CH:45]=[CH:46][S:47][C:30]=3[C:29](=[O:28])[N:35]3[CH2:36][CH2:37][C@H:34]3[C:33]=12)=[O:42])=[O:15]

Participants

5

Reactant 3

HCID 20825N-PhthaloylglycineHCID 682631,1'-CarbonyldiimidazoleHCID 67713661HCID 67713661, compound

Product 1

HCID 67713642HCID 67713642, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5.8 g (19 mmol) of N-phthaloylglycine in 30 ml of dimethylformamide was treated at room temperature with 3.2 g (19.75 mmol) of 1,1'-carbonyldiimidazole and the mixture was subsequently heated to 50°. After 30 minutes the mixture was cooled to room temperature, 5.6 g (19.63 mmol) of (S)-8-oxo-11,11 a-dihydro-8H,10H-azeto[1,2-a]imidazo[5,1-c]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 colour-less powder obtained was washed with ethanol and diethyl ether. There were obtained 8.7 g (96%) of (S)-N'-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-ylacetyl)-8-oxo-11,11a-dihydro-8H,10H-azeto [1,2-a]imidazo[5,1-c]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 colour-less powder obtained
  5. washwas washed with ethanol and diethyl ether

Sources & evidence

ORD record
ord-8c56a6b78cbc493ab31fa77a7af5a6bf
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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