Hydrochloric Acid → HCID 178435497, compound

HRID 1064560Notes

Reaction equation

[CH3:1][CH2:2][C:3]1[C:24]([CH3:25])=[C:23]2[NH:26][C:4]=1[CH:5]=[C:6]1[N:10]=[C:9]([C:11]([CH:38]=[O:39])=[C:12]3[N:16]=[C:15]([CH:17]=[C:18]4[NH:27][C:21](=[CH:22]2)[C:20]([CH:28]=[CH2:29])=[C:19]4[CH3:30])[C@@H:14]([CH3:31])[C@@H:13]3[CH2:32][CH2:33][C:34]([O:36]C)=[O:35])[C:8]([C:40]([O:42]C)=[O:41])=[C:7]1[CH3:44].Cl>CC(C)=O>[CH3:1][CH2:2][C:3]1[C:24]([CH3:25])=[C:23]2[NH:26][C:4]=1[CH:5]=[C:6]1[N:10]=[C:9]([C:11]([CH:38]=[O:39])=[C:12]3[N:16]=[C:15]([CH:17]=[C:18]4[NH:27][C:21](=[CH:22]2)[C:20]([CH:28]=[CH2:29])=[C:19]4[CH3:30])[C@@H:14]([CH3:31])[C@@H:13]3[CH2:32][CH2:33][C:34]([OH:36])=[O:35])[C:8]([C:40]([OH:42])=[O:41])=[C:7]1[CH3:44]

Participants

Conditions

Temperature: 25 °C

Procedure

Purpurin 5 dimethyl ester is dissolved in acetone and concentrated hydrochloric acid (37%) is added in the ratio 1:2. The mixture is stirred for 2 hours at 25° C., neutralised, purpurin 5 is filtered out, washed with water, dissolved in 10 % N-methyl-D-glucamine solution and gel filtrated on a Sephadex G10 column with the use of 1% N-methyl-D-glucamine solution as an eluent, the second fraction is collected, neutralised, a precipitate is filtered out, washed with water, dried over phosphorus pentoxide till the weight becomes constant to give purpurin 5 (5.2% calculating to the dry reaction mass taken for esterification).

Workup

filtrationneutralised, purpurin 5 is filtered out
washwashed with water
dissolutiondissolved in 10 % N-methyl-D-glucamine solution
filtrationgel filtrated on a Sephadex G10 column with the use of 1% N-methyl-D-glucamine solution as an eluent
customthe second fraction is collected
filtrationa precipitate is filtered out
washwashed with water
dry with materialdried over phosphorus pentoxide till the weight

Sources & evidence

ORD record: ord-b2312bf628644166994c85a790fbae46
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06969765B2

Reaction notes

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