Sodium Carbonate → HCID 67652588, compound

HRID 976022Notes

Reaction equation

[NH2:1][C@@H:2]([CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@H:10]([NH2:14])[C:11]([OH:13])=[O:12])[C:3]([OH:5])=[O:4].[C:15]([O-:18])([O-:17])=O.[Na+].[Na+].[C:21](Cl)([O:23][CH2:24][CH:25]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]2[C:26]1=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22]>O.O1CCOCC1>[CH:27]1[C:26]2[CH:25]([CH2:24][O:17][C:15]([NH:1][C@@H:2]([CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@H:10]([NH:14][C:21]([O:23][CH2:24][CH:25]3[C:37]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[C:31]4[C:26]3=[CH:27][CH:28]=[CH:29][CH:30]=4)=[O:22])[C:11]([OH:13])=[O:12])[C:3]([OH:5])=[O:4])=[O:18])[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31]=2[CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(S,S)-2,7-Diamino-Z-oct-4-enedioic acid (0.050 g, 0.25 mmol) and Na2CO3 (0.21 g, 20.0 mmol) were dissolved in 3 ml water and 2 ml dioxane. The solution was cooled to 0° C. and a solution of FmocCl (0.26 g, 1.0 mmol) in 1 ml dioxane was added. This mixture was stirred at 0° C. for 3 hours and came to ambient temperature overnight. After extraction with diethyl ether it was acidified by addition of hydrochloric acid. The solution was extracted with chloroform and the amino acid was crystallized from chloroform/hexane. The compound was further purified by flash chromatography (chloroform/acetic acid 9/1).

Workup

waitcame to ambient temperature overnight
extractionAfter extraction with diethyl ether it
additionwas acidified by addition of hydrochloric acid
extractionThe solution was extracted with chloroform
customthe amino acid was crystallized from chloroform/hexane
customThe compound was further purified by flash chromatography (chloroform/acetic acid 9/1)

Sources & evidence

ORD record: ord-e729d0bcb3444deb9584a6b56a95b187
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05610141

Reaction notes

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