Benzyl Alcohol → (S)-2-(2-(benzyloxy)-7-bromo-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate

HRID 1468712Notes

Reaction equation

HRID 1468712 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O(CC1C=CC=CC=1)[Na].[C:20]([O:26][CH2:27][C@H:28]([C:34]1[C:43]([CH3:44])=[CH:42][C:37]2[N:38]=[C:39](Cl)[S:40][C:36]=2[C:35]=1[Br:45])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])(=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22]>>[C:20]([O:26][CH2:27][C@H:28]([C:34]1[C:43]([CH3:44])=[CH:42][C:37]2[N:38]=[C:39]([O:10][CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[S:40][C:36]=2[C:35]=1[Br:45])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])(=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 4

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 70981474(S)-2-(7-bromo-2-chloro-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalateHCID 178507099HCID 178507099, compound

Product 1

HCID 70981768(S)-2-(2-(benzyloxy)-7-bromo-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate

Procedure

NaH (415 mg, 10.38 mmol) was added to BnOH, stirred at rt for 0.5 h. The NaOBn solution was transferred to a flask charged with (S)-2-(7-bromo-2-chloro-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate (65I) (1.6 g, 3.46 mmol). The reaction mixture was heated at 60° C. for 45 min. The reaction mixture was washed by sat NaHCO3, extracted by EtOAc, the organic phase was washed by brine, dry over MgSO4, filtered, concentrated down, distilled most NaOH off. The residue was purified by silica gel column, eluting by 0-50% EtOAc in hexanes.

Workup

  1. temperatureThe reaction mixture was heated at 60° C. for 45 min
  2. washThe reaction mixture was washed
  3. extractionextracted by EtOAc
  4. washthe organic phase was washed by brine
  5. dry with materialdry over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated down
  8. distillationdistilled most NaOH off
  9. customThe residue was purified by silica gel column
  10. washeluting by 0-50% EtOAc in hexanes

Sources & evidence

ORD record
ord-cdda1012e7f54765a26f1acf68c63e59
Source dataset
uspto-grants-2015_04
Patent number
US09006229B2

Reaction notes

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