Potassium Carbonate → HCID 88605402, compound

HRID 2107845Notes

Reaction equation

[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:26]/[O:27][C:28]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)/[C:8]([NH:10][CH:11]2[C:24](=[O:25])[N:13]3[C:14]([C:21]([OH:23])=[O:22])=[C:15](/[CH:18]=[CH:19]\[CH3:20])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.C([O-])([O-])=O.[K+].[K+].[C:53]([O:56][CH:57](Br)[CH3:58])(=[O:55])[CH3:54].C([O-])(O)=O.[Na+]>CN(C=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:26]/[O:27][C:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)/[C:8]([NH:10][CH:11]2[C:24](=[O:25])[N:13]3[C:14]([C:21]([O:23][CH:57]([O:56][C:53](=[O:55])[CH3:54])[CH3:58])=[O:22])=[C:15](/[CH:18]=[CH:19]\[CH3:20])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

Conditions

Temperature: 5 °C

Procedure

To a cooled solution of the product of Procedure 7 (34.4 g, 52.8 mmol) and well-milled K2CO3 (7.24 g, 52.8 mmol) in dry DMF (344 ml) was added 1-acetoxyethyl bromide (17.64 g, 105.6 mmol) at 0° C. under argon and the mixture was stirred at about 5° C. for 65 min. The reaction mixture was poured into ice-water (1720 ml) with stirring adjusted to pH 7 with aq. NaHCO3 solution, and stirred for 30 min. The resulting precipitate was collected, washed with water (100 ml) and dried to give 37.61 g of the desired product (97%, purity 80%) as an amorphous powder.

Workup

stirringwith stirring
stirringstirred for 30 min
customThe resulting precipitate was collected
washwashed with water (100 ml)
customdried

Sources & evidence

ORD record: ord-0ff148e766e047fda35682eb7e6864cc
Source dataset: uspto-grants-1990_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04935508

Reaction notes

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