Dimethyl Sulfide → HDTrp-Leu-MetNH2 acetate

HRID 2418580Notes

Reaction equation

[NH:1](C(OC(C)(C)C)=O)[C@@H:2]([C:13]([NH:15][C@H:16]([C:21]([NH:23][C@H:24]([C:29]([NH2:31])=[O:30])[CH2:25][CH2:26][S:27][CH3:28])=[O:22])[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.F[C:40](F)(F)[C:41]([OH:43])=[O:42].CSC>C(S)(S)C>[NH2:1][C@@H:2]([C:13]([NH:15][C@H:16]([C:21]([NH:23][C@H:24]([C:29]([NH2:31])=[O:30])[CH2:25][CH2:26][S:27][CH3:28])=[O:22])[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[CH3:40][C:41]([OH:43])=[O:42]

Participants

Conditions

Temperature: 0 °C

Procedure

BocDTrp-Leu-MetNH2 (47.5 mmole) was added to a solution of trifluoroacetic acid (230 ml.), dimethylsulfide (260 ml.) and ethanedithiol (20 ml.) with cooling to 0° C. The mixture was allowed to warm to room temperature during one and one half hours, then stripped of volatiles. Attempted crystallization of the residue from ethyl acetate-hexane was unsuccessful, and the mixture was stripped again. The residue was dissolved in methanol-ether. Removal of a small amount (about 300 mg.) of solid and addition of acetic acid to the filtrate afforded HDTrp-Leu-MetNH2 acetate salt in 60% yield (12.6 g., m.r. 154°-160° C.).

Workup

temperatureto warm to room temperature during one and one half hours
customAttempted crystallization of the residue from ethyl acetate-hexane
dissolutionThe residue was dissolved in methanol-ether
customRemoval of a small amount (about 300 mg.) of solid and addition of acetic acid to the filtrate

Sources & evidence

ORD record: ord-44a0878929824814a91e05a9d2694fde
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04472305

Reaction notes

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