2-Thiophenecarboxylic acid → HCID 58826473, compound

HRID 2244671Notes

Reaction equation

HRID 2244671 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@H:8]([OH:10])[C@@H:7]([NH2:11])[CH2:6]1)=[O:4].[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17](O)=[O:18].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:6][C@H:7]([NH:11][C:17]([C:13]2[S:12][CH:16]=[CH:15][CH:14]=2)=[O:18])[C@@H:8]([OH:10])[CH2:9]1)=[O:4]

Participants

6

Reactant 3

HCID 107002-Thiophenecarboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 58826449HCID 58826449, compound

Product 1

HCID 58826473HCID 58826473, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of the (1R,3S,4S)-3-amino-4-hydroxy-cyclopentanecarboxylic acid methyl ester (300 mg) at r.t. in DMF (7.0 ml) under an argon atmosphere were added N-ethyldiisopropylmine (0.96 ml), 2-thiophene carboxylic acid (314 mg) and BOP (1.04 g). The mixture was then stirred at r.t. for 19 h. The clear brown solution was diluted with EtOAc and washed with H2O. The aqueous phase was back extracted with EtOAc. The combined organics were washed with H2O and brine, dried (MgSO4), filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient: cyclohexane→cyclohexane/EtOAc 1:1) to give (1R,3S,4S)-3-hydroxy-4-[(thiophene-2-carbonyl)-amino]-cyclopentanecarboxylic acid methyl ester as light brown gum. MS: 270.3 ([M+H]+).

Workup

  1. washwashed with H2O
  2. extractionThe aqueous phase was back extracted with EtOAc
  3. washThe combined organics were washed with H2O and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (silica gel; gradient: cyclohexane→cyclohexane/EtOAc 1:1)

Sources & evidence

ORD record
ord-a4772a4b4b4a4418b59fbdc879db9467
Source dataset
uspto-grants-2010_03
Patent number
US07678917B2

Reaction notes

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