(3R,4R)-4-(4-(Benzyloxy)phenylsulfonamido)-N-tert-butoxy-3-methyl-tetrahydro-2H-pyran-3-carboxamide → (3R,4R)-N-tert-butoxy-4-(4-hydroxyphenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxamide

HRID 736786Notes

Reaction equation

HRID 736786 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C@@H:19]2[CH2:24][CH2:23][O:22][CH2:21][C@:20]2([CH3:33])[C:25]([NH:27][O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:26])(=[O:17])=[O:16])=[CH:11][CH:10]=1)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[C:29]([O:28][NH:27][C:25]([C@:20]1([CH3:33])[C@H:19]([NH:18][S:15]([C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)(=[O:17])=[O:16])[CH2:24][CH2:23][O:22][CH2:21]1)=[O:26])([CH3:32])([CH3:30])[CH3:31]

Participants

4

Reactant 1

HCID 86607886(3R,4R)-4-(4-(Benzyloxy)phenylsulfonamido)-N-tert-butoxy-3-methyl-tetrahydro-2H-pyran-3-carboxamide

Product 1

HCID 86607887(3R,4R)-N-tert-butoxy-4-(4-hydroxyphenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(3R,4R)-4-(4-(Benzyloxy)phenylsulfonamido)-N-tert-butoxy-3-methyl-tetrahydro-2H-pyran-3-carboxamide was dissolved in ethyl acetate (25 mL), 10% palladium on carbon (90 mg) was added, and the resulting reaction mixture was stirred under a hydrogen balloon overnight. The reaction mixture was then filtered and concentrated to provide (3R,4R)-N-tert-butoxy-4-(4-hydroxyphenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxamide as a white solid that was used in the next step without purification. MS: (M+Na)+=409.0; (M−H)−=385.2.

Workup

  1. customthe resulting reaction mixture
  2. filtrationThe reaction mixture was then filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e66282e8254d44d1aeed7e8b30119043
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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