Sodium Carbonate → N,N'-Bis{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-cystine

HRID 2112112Notes

Reaction equation

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

Participants

Conditions

Temperature: 10 °C

Procedure

Fmoc-protected cysteine (FIG. 3, structure B) was synthesized in a two step sequence from L-cystine as outlined in FIG. 4. Sodium carbonate (4.6 g, 43.6 mmol) and L-cystine (5.0 g, 20.8 mmol) were dissolved in water (200 mL). The resulting solution was cooled to 10° C. FmocCl (11.85 g, 45.8 mmol) was dissolved in dioxane (80 mL), and the resulting solution was added dropwise to the aqueous solution of L-cystine. The solution was stirred for 2 h at 10° C. and allowed to gradually warm to room temperature. A thick white precipitate was obtained that was filtered onto a sintered glass funnel. The product was triturated with diethyl ether (50 mL) and dried in vacuuo for 2 d. N,N′-Bis(Fmoc)-L-cystine (14.0 g, 98% yield) was obtained as a white powder.

Workup

temperatureto gradually warm to room temperature
customA thick white precipitate was obtained
filtrationthat was filtered onto a sintered glass funnel
customThe product was triturated with diethyl ether (50 mL)
customdried in vacuuo for 2 d

Sources & evidence

ORD record: ord-6c2c8cf64d0f4526ad3abe6ffe9eac9b
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07521529B2

Reaction notes

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