Water → HCID 15232557, compound

HRID 1109793Notes

Reaction equation

HRID 1109793 reaction equation
[OH:1][CH:2]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:3]#[C:4][C:5]([CH3:18])([NH:7][S:8]([C:11]1[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=1)(=[O:10])=[O:9])[CH3:6].C([Mg]Br)C.Cl[C:31]([O:33][CH3:34])=[O:32].O>C1COCC1>[CH3:34][O:33][C:31]([O:1][CH:2]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:3]#[C:4][C:5]([CH3:6])([NH:7][S:8]([C:11]1[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=1)(=[O:10])=[O:9])[CH3:18])=[O:32]

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 15232556HCID 15232556, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 15232557HCID 15232557, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 10 ml of THF was dissolved 1.37 g (3.76 mmole) of the 5-hydroxy-2-methyl-2-tosylamino-3-dodecyne obtained in Reference Example 1, and a THF solution of ethylmagnesium bromide (8.27 mmole) was added thereto, followed by stirring for 40 minutes. To the mixture was added dropwise 0.668 ml (8.65 mmole) of methyl chloroformate, and stirring was further continued for 50 minutes. Water was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed successively with a hydrochloric acid aqueous solution, a sodium hydrogencarbonate aqueous solution, and water, and then dried. The solvent was removed by distillation, and the residual oily substance was purified by column chromatography to obtain 1.37 g (percent yield: 86%) of 5-methoxycarbonyloxy-2-methyl-2-tosylamino-3-dodecyne.

Workup

  1. customobtained in Reference Example 1
  2. stirringstirring
  3. waitwas further continued for 50 minutes
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed successively with a hydrochloric acid aqueous solution
  6. dry with materiala sodium hydrogencarbonate aqueous solution, and water, and then dried
  7. customThe solvent was removed by distillation
  8. customthe residual oily substance was purified by column chromatography

Sources & evidence

ORD record
ord-721fbc4a5f444b84b50023214c6f4fda
Source dataset
uspto-grants-1994_06
Patent number
US05322939

Reaction notes

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