Sodium Hydroxide → (1R,3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-hydroxy-cyclopentanecarboxylic acid

HRID 2244684Notes

Reaction equation

HRID 2244684 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:9][C@H:8]([OH:10])[C@@H:7]([NH:11][C:12]([C:14]2[S:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[O:13])[CH2:6]1)=[O:4].[OH-].[Na+]>CO>[Cl:19][C:16]1[S:15][C:14]([C:12]([NH:11][C@@H:7]2[C@@H:8]([OH:10])[CH2:9][C@H:5]([C:3]([OH:4])=[O:2])[CH2:6]2)=[O:13])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58826431(1R,3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-hydroxy-cyclopentanecarboxylic acid methyl ester

Product 1

HCID 58826452(1R,3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-hydroxy-cyclopentanecarboxylic acidYield 75.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of (1R,3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-hydroxy-cyclopentanecarboxylic acid methyl ester (611 mg; example 1B) in MeOH (4 ml) was added 1N NaOH (4 ml). The reaction mixture which slowly turned into a clear solution was stirred at r.t. for 2 hrs, then concentrated. The residue was dissolved in H2O and washed with Et2O. The aqueous phase was acidified with 3N HCl, then extracted with CH2Cl2/MeOH 9:1. The combined organic layers were washed with H2O and brine, dried over MgSO4 and concentrated to give (1R,3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-hydroxy-cyclopentanecarboxylic acid (442 mg) as off-white solid. MS: 288.0 ([M−H]−).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in H2O
  3. washwashed with Et2O
  4. extractionextracted with CH2Cl2/MeOH 9:1
  5. washThe combined organic layers were washed with H2O and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8e827d1b0905425d8adf9c970ebfde46
Source dataset
uspto-grants-2010_03
Patent number
US07678917B2

Reaction notes

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