(S)-2-(2-(benzyloxy)-7-bromo-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate → HCID 178422341, compound

HRID 1468713Notes

Reaction equation

HRID 1468713 reaction equation
[C:1]([O:7][CH2:8][C@H:9]([C:15]1[C:31]([CH3:32])=[CH:30][C:18]2[N:19]=[C:20]([O:22]CC3C=CC=CC=3)[S:21][C:17]=2[C:16]=1[Br:33])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]>CCOC(C)=O.CCO.[Pd]>[C:1]([O:7][CH2:8][C@H:9]([C:15]1[C:31]([CH3:32])=[CH:30][C:18]2[N:19]=[C:20]([OH:22])[S:21][C:17]=2[C:16]=1[Br:33])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:6])[C:2]([CH3:3])([CH3:4])[CH3:5]

Participants

4

Reactant 1

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

Product 1

HCID 178422341HCID 178422341, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

The mixture of (S)-2-(2-(benzyloxy)-7-bromo-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate (67A), Pd/C (800 mg) in EtOAc/EtOH (10 ml, 1:1) was charged into a flask with H2 balloon, and stirred at rt for 1 h. The reaction mixture was filtered over celite, concentrated down, purified by silica gel column, eluting by 0-50% EtOAc in hexanes to give 67B (850 mg).

Workup

  1. additionwas charged into a flask with H2 balloon
  2. filtrationThe reaction mixture was filtered over celite
  3. concentrationconcentrated down
  4. custompurified by silica gel column
  5. washeluting by 0-50% EtOAc in hexanes

Sources & evidence

ORD record
ord-a5255473bef2440f94d9f74746cb1732
Source dataset
uspto-grants-2015_04
Patent number
US09006229B2

Reaction notes

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