(2S,4S)-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-2-oxazol-2-yl-pyrrolidine-1-carboxylic acid benzyl ester → 1-hydroxy-naphthalene-2-carboxylic acid ((3S,5S)-5-oxazol-2-yl-pyrrolidin-3-yl)-amide

HRID 1477561Notes

Reaction equation

HRID 1477561 reaction equation
C(OC([N:11]1[CH2:15][C@@H:14]([NH:16][C:17]([C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[OH:29])=[O:18])[CH2:13][C@H:12]1[C:30]1[O:31][CH:32]=[CH:33][N:34]=1)=O)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[O:31]1[CH:32]=[CH:33][N:34]=[C:30]1[C@H:12]1[NH:11][CH2:15][C@@H:14]([NH:16][C:17]([C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[OH:29])=[O:18])[CH2:13]1

Participants

4

Reactant 1

HCID 89768897(2S,4S)-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-2-oxazol-2-yl-pyrrolidine-1-carboxylic acid benzyl ester

Product 1

HCID 897762371-hydroxy-naphthalene-2-carboxylic acid ((3S,5S)-5-oxazol-2-yl-pyrrolidin-3-yl)-amideYield 77.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of (2S,4S)-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-2-oxazol-2-yl-pyrrolidine-1-carboxylic acid benzyl ester (30 mg, 0.06 mmol) in methanol (2 mL) was added 20% Pd(OH)2 (20 mg) and the mixture was stirred at room temp. for 16 h. with a balloon containing H2 gas. The reaction mixture was then filtered and concentrated under reduced pressure to give 1-hydroxy-naphthalene-2-carboxylic acid ((3S,5S)-5-oxazol-2-yl-pyrrolidin-3-yl)-amide (15 mg) as a light brown liquid. MS calcd. for C18H18N3O3[(M+H)+] 324, obsd. 324.

Workup

  1. additioncontaining H2 gas
  2. filtrationThe reaction mixture was then filtered
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-167ed63cc8b74f27a838f2a5d654ac52
Source dataset
uspto-grants-2016_08
Patent number
US09403805B2

Reaction notes

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