Methyl iodide → HCID 88657694, compound

HRID 2118635Notes

Reaction equation

[NH:1]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@@H:2]([C:7]([NH:9][C@H:10]([C:15]([O:17][CH3:18])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][CH2:4][S:5][CH3:6].C[I:27]>>[I-:27].[CH3:4][SH2+:5].[CH3:18][O:17][C:15](=[O:16])[C@H:10]([CH2:11][CH:12]([CH3:13])[CH3:14])[NH:9][C:7](=[O:8])[C@@H:2]([CH2:3][CH2:4][S:5][CH3:6])[NH:1][C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20]

Participants

Reactant 2

HCID 6328Methyl iodide

HCID 10022430HCID 10022430, compound

Product 1

HCID 88657694HCID 88657694, compoundYield 103%

Procedure

Boc-D-Met-Leu-OCH3 (25 g, 66.5 mmol) was dissolved in methyl iodide (132 ml) and stirred at room temperature for 2 days. Concentration in vacuo gave 35.4 g (103%) of the sulfonium salt. The nmr spectrum was consistent with the proposed structure.

Workup

concentrationConcentration in vacuo

Sources & evidence

ORD record: ord-73f45ec087d64ade89582b65d54774be
Source dataset: uspto-grants-1987_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04680283

Reaction notes

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