Methyl iodide → HCID 15107593, compound

HRID 1609485Notes

Reaction equation

HRID 1609485 reaction equation
[C:1]([N:8]1[C@@H:12]([CH2:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C@H:11]([CH2:20][CH:21]2[S:26](=[O:28])(=[O:27])[CH2:25][CH2:24][CH2:23][S:22]2(=[O:30])=[O:29])[O:10][C:9]1([CH3:32])[CH3:31])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:33]I>C1COCC1.CCCCCC.CCOCC>[C:1]([N:8]1[C@@H:12]([CH2:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C@H:11]([CH2:20][C:21]2([CH3:33])[S:26](=[O:27])(=[O:28])[CH2:25][CH2:24][CH2:23][S:22]2(=[O:30])=[O:29])[O:10][C:9]1([CH3:32])[CH3:31])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 2

HCID 6328Methyl iodideHCID 15107583HCID 15107583, compound

Product 1

HCID 15107593HCID 15107593, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of 0.98 g of 2-[(4S,5S)-3-BOC-4-cyclohexylmethyl-2,2-dimethyl-5-oxazolidinyl-methyl]-1,3-dithiane 1,1,3,3-tetroxide in 300 ml of THF is mixed at -30° with 1.3 ml of a 1.6 molar solution of butyl-Li in hexane. The mixture is stirred for 1 h and then 0.56 g of methyl iodide is added and the mixture is stirred for 24 h in a thawing cooled bath, diluted with 50 ml of ether, and worked up as usual to give 2-[(4S,5S)-3-BOC-4-cyclohexylmethyl-2,2-dimethyl-5-oxazolidinyl-methyl]-2-methyl-l,3-dithiane 1,1,3,3-tetroxide, m.p. 176°-177°.

Workup

  1. stirringthe mixture is stirred for 24 h in a thawing
  2. temperaturecooled bath

Sources & evidence

ORD record
ord-2d0f87eb1bbf463a9a371b019c664f49
Source dataset
uspto-grants-1995_03
Patent number
US05401722

Reaction notes

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