4-Toluenesulfonyl chloride → HCID 59201644, compound

HRID 451882Notes

Reaction equation

HRID 451882 reaction equation
[CH2:1]1[C:3]2([CH2:8][CH2:7][C@H:6]([CH2:9][C@H:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:11][OH:12])[CH2:5][O:4]2)[CH2:2]1.[S:21](Cl)([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)(=[O:23])=[O:22]>N1C=CC=CC=1>[CH3:28][C:27]1[CH:29]=[CH:30][C:24]([S:21]([O:12][CH2:11][C@@H:10]([NH:13][C:14]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:20])[CH2:9][C@H:6]2[CH2:7][CH2:8][C:3]3([CH2:2][CH2:1]3)[O:4][CH2:5]2)(=[O:23])=[O:22])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 59201744HCID 59201744, compound

Product 1

HCID 59201644HCID 59201644, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The tert-butyl (S)-1-((R)-4-oxaspiro[2.5]oct-6-yl)-3-hydroxypropan-2-ylcarbamate (1.70 g, 5.92 mmol) and tosyl chloride (4.5 g, 23.7 mmol, 4.0 equiv) were dissolved in pyridine (30 mL) and the mixture stirred at room temperature for 17 hr. The pyridine was removed in vacuo and the residue partitioned between EtOAc and 1.0 M HCl. The layers were separated and the organic layer washed with brine, dried over Na2SO4, filtered and evaporated. The (S)-2-(tert-butoxycarbonylamino)-3-((R)-4-oxaspiro[2.5]oct-6-yl)propyl 4-methylbenzenesulfonate was purified by flash chromatography on silica eluting with 0-29% EtOAc in hexanes. The fractions were evaporated and used directly in the next step. MS ESI +ve m/z 464 (M+Na).

Workup

  1. customThe pyridine was removed in vacuo
  2. customthe residue partitioned between EtOAc and 1.0 M HCl
  3. customThe layers were separated
  4. washthe organic layer washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe (S)-2-(tert-butoxycarbonylamino)-3-((R)-4-oxaspiro[2.5]oct-6-yl)propyl 4-methylbenzenesulfonate was purified by flash chromatography on silica eluting with 0-29% EtOAc in hexanes
  9. customThe fractions were evaporated

Sources & evidence

ORD record
ord-2d761213fc324b38a807358bcf59f86e
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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