Diisopropylethylamine → (1R,3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-hydroxy-cyclopentanecarboxylic acid methyl ester
Reaction equation
Cl.[CH3:2][O:3][C:4]([C@H:6]1[CH2:10][C@H:9]([OH:11])[C@@H:8]([NH2:12])[CH2:7]1)=[O:5].C(N(C(C)C)C(C)C)C.[Cl:22][C:23]1[S:27][C:26]([C:28](O)=[O:29])=[CH:25][CH:24]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C1COCC1>[CH3:2][O:3][C:4]([C@H:6]1[CH2:10][C@H:9]([OH:11])[C@@H:8]([NH:12][C:28]([C:26]2[S:27][C:23]([Cl:22])=[CH:24][CH:25]=2)=[O:29])[CH2:7]1)=[O:5]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (1R,3S,4S)-3-amino-4-hydroxy-cyclopentanecarboxylic acid methyl ester hydrochloride (160 mg) in THF (5 ml) was treated under an argon atmosphere with N-ethyldiisopropylamine (0.56 ml), 5-chloro-2-thiophenecarboxylic acid (160 mg) and BOP (434 mg). The mixture soon turned to a clear light yellow solution and was then stirred for 18 h. The reaction mixture was concentrated. The crude product was purified by chromatography (silica gel; gradient: cyclohexane→cyclohexane/EtOAc 3:7) to give (1R,3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-hydroxy-cyclopentane-carboxylic acid methyl ester as colorless gum. MS: 304.0 ([M+H]+).
Workup
- concentrationThe reaction mixture was concentrated
- customThe crude product was purified by chromatography (silica gel; gradient: cyclohexane→cyclohexane/EtOAc 3:7)
Sources & evidence
- ORD record
- ord-5e6e8c049b0d4bcb9bdfcfa61e0287ee
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07678917B2
Reaction notes
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