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

HRID 2244662
ノート
印刷プレビュー

反応式

HRID 2244662 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 950485-Chloro-2-thiophenecarboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 68685176Methyl (1R,3S,4S)-3-amino-4-hydroxycyclopentane-1-carboxylate hydrochloride

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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]+).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customThe crude product was purified by chromatography (silica gel; gradient: cyclohexane→cyclohexane/EtOAc 3:7)

出典と根拠

ORDレコード
ord-5e6e8c049b0d4bcb9bdfcfa61e0287ee
出典データセット
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07678917B2

反応ノート

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