Iodomethyl pivalate → HCID 53920308, compound

HRID 1005544Notes

Reaction equation

[C:1]([O:8][CH2:9][CH2:10][O:11][CH2:12][N:13]1[C:17]([S:18][C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)=[C:16]([CH:27]([CH3:29])[CH3:28])[N:15]=[C:14]1[CH3:30])(=[O:7])[CH2:2][CH2:3][C:4]([O-:6])=[O:5].[C:31]([O:37][CH2:38]I)(=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33]>>[C:1]([O:8][CH2:9][CH2:10][O:11][CH2:12][N:13]1[C:17]([S:18][C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)=[C:16]([CH:27]([CH3:28])[CH3:29])[N:15]=[C:14]1[CH3:30])(=[O:7])[CH2:2][CH2:3][C:4]([O:6][CH2:38][O:37][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])=[O:5]

Participants

Reactant 2

HCID 104401Iodomethyl pivalate

HCID 86755354HCID 86755354, compound

Product 1

HCID 53920308HCID 53920308, compoundYield 84.5%

Procedure

The compound 76 (250 mg, 0.526 mmol) was converted to the ester with pivaloyloxymethyl iodide (140 mg, 0.578 mmol) under potassium carbonate (50.9 mg, 0.368 mmol) in the same manner as the example 61 to give the compound 78 (262 mg, 84%) as oil. Rf 0.18 (1:1 EtOAc - hexane).

Sources & evidence

ORD record: ord-dfaf6ceb77aa4d97be94fc72f96a0b0c
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06054591

Reaction notes

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