Tetrahydrofuran → tert-butyl ((2S)-1-((2-(4-hydroxyphenyl)[1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)carbamate

HRID 2277338Notes

Reaction equation

HRID 2277338 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[CH:22]=[C:21]([O:23][CH2:24][C@@H:25]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH3:26])[N:20]=[CH:19][C:18]=3[N:35]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C1COCC1>[Pd].CN(C=O)C>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[CH:22]=[C:21]([O:23][CH2:24][C@@H:25]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:32])([CH3:31])[CH3:33])[CH3:26])[N:20]=[CH:19][C:18]=3[N:35]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 86731321tert-butyl ((2S)-1-((2-(4-(benzyloxy)phenyl) [1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)carbamate

Product 1

HCID 136341411tert-butyl ((2S)-1-((2-(4-hydroxyphenyl)[1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)carbamateYield 71.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of tert-butyl ((2S)-1-((2-(4-(benzyloxy)phenyl) [1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)carbamate (2.5 g), 10% palladium/carbon (containing water (50%), 0.5 g), THF (200 mL) and DMF (50 mL) was stirred for 15 hr under a hydrogen atmosphere. The catalyst was removed by filtration, and the obtained filtrate was concentrated under reduced pressure. The obtained solid was collected by filtration, washed with hexane/ethyl acetate (4/1), dried to give the title compound (1.45 g).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe obtained filtrate was concentrated under reduced pressure
  3. filtrationThe obtained solid was collected by filtration
  4. washwashed with hexane/ethyl acetate (4/1)
  5. customdried

Sources & evidence

ORD record
ord-0234e7209f6f4b2da69023dc5a3ea261
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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