Sodium Bicarbonate → HCID 19785836, compound

HRID 256723Notes

Reaction equation

[OH:1][CH2:2][CH2:3][O:4][C:5]([NH:7][CH2:8][CH2:9][N:10]([C:20]1[N:25]=[C:24]([N:26]([CH2:36][CH2:37][NH:38][C:39]([O:41][CH2:42][CH2:43][OH:44])=[O:40])[CH2:27][CH2:28][NH:29][C:30]([O:32][CH2:33][CH2:34][OH:35])=[O:31])[N:23]=[C:22](Cl)[N:21]=1)[CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][CH2:18][OH:19])=[O:15])=[O:6].[C:46](=[O:49])([OH:48])[O-].[Na+]>C(O)CO>[OH:1][CH2:2][CH2:3][O:4][C:5]([NH:7][CH2:8][CH2:9][N:10]([CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][CH2:18][OH:19])=[O:15])[C:20]1[N:25]=[C:24]([N:26]([CH2:36][CH2:37][NH:38][C:39]([O:41][CH2:42][CH2:43][OH:44])=[O:40])[CH2:27][CH2:28][NH:29][C:30]([O:32][CH2:33][CH2:34][OH:35])=[O:31])[N:23]=[C:22]([N:10]([CH2:9][CH2:8][NH:7][C:5]([O:4][CH2:3][CH2:2][OH:1])=[O:6])[CH2:11][CH2:12][NH:13][C:46]([O:48][CH2:18][CH2:17][OH:16])=[O:49])[N:21]=1)=[O:6]

Participants

Conditions

Temperature: 115 °C

Procedure

To 6.7 g of (I) (Example 1, TECT) were added 2.8 g HEC, 0.84 g sodium bicarbonate and 25 g ethylene glycol. The reaction mixture was then heated to 115° C. in an oil bath for 4 hours, after which most of the HEC had reacted with TECT as indicated by amine titration of the reaction mixture. Ethyelene glycol was distilled off under reduced pressure. The residue was poured into methanol. Separated solids were filtered and recrystallized from methanol. Yield 5.6 g (60% of theoretical), m.p. 192° C. The nmr and fab mass spectra confirmed the product to be of FORMULA II: ##STR18##

Workup

customafter which most of the HEC had reacted with TECT
distillationEthyelene glycol was distilled off under reduced pressure
additionThe residue was poured into methanol
customSeparated solids
filtrationwere filtered
customrecrystallized from methanol

Sources & evidence

ORD record: ord-ce30e56043b54ce694321c2730408841
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05258514

Reaction notes

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