Sodium Carbonate → HCID 22876609, compound

HRID 1378252Notes

Reaction equation

HRID 1378252 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]([NH:15][NH:16][C:17]([C:19]1[N:20]=[CH:21][N:22]2[C:28]3[CH:29]=[CH:30][S:31][C:27]=3[C:26](=[O:32])[N:25]3[CH2:33][CH2:34][CH2:35][C@H:24]3[C:23]=12)=O)=[O:14].C(=O)([O-])[O-].[Na+].[Na+]>>[O:32]=[C:26]1[N:25]2[CH2:33][CH2:34][CH2:35][C@H:24]2[C:23]2=[C:19]([C:17]3[O:14][C:13]([CH2:12][N:3]4[C:4](=[O:11])[C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[C:2]4=[O:1])=[N:15][N:16]=3)[N:20]=[CH:21][N:22]2[C:28]2[CH:29]=[CH:30][S:31][C:27]1=2

Participants

3

Reactant 2

HCID 10340Sodium CarbonateHCID 67713329HCID 67713329, compound

Product 1

HCID 22876609HCID 22876609, compoundYield 78%

Procedure

A solution of 10 g (20.4 mmol) 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 in 90 g of polyphosphoric acid was stirred at 100° for 1.5 hours. After cooling to room temperature the mixture was poured into 300 ml of ice-water while stirring well, whereupon solid sodium carbonate was added to pH=8. Extraction with methylene chloride and chromatography (silica gel, methylene chloride/methanol 20:1) yielded 7.5 g (78%) of (S)-2-[5-(8-oxo-10,11,12,12a-tetrahydro-8H-imidazo[5,1-c]pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepin-1-yl)-1,3,4-oxadiazol-2-ylmethyl ]-2.3-dihydro-1H-isoindole-1,3-dione as a colourless powder of m.p. >250.

Workup

  1. additionwas added to pH=8
  2. extractionExtraction with methylene chloride and chromatography (silica gel, methylene chloride/methanol 20:1)

Sources & evidence

ORD record
ord-d08dbc00fc934e27b1686e42e49e7b5c
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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