5-Chloro-2-nitrobenzoic acid → HCID 57725370、化合物

HRID 1091433ノート

反応式

HRID 1091433 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.Cl.[C:15]([O:19][C:20](=[O:25])[C@@H:21]([NH2:24])[CH2:22][CH3:23])([CH3:18])([CH3:17])[CH3:16].C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>O1CCCC1.CN(C1C=CN=CC=1)C.C(Cl)CCl>[C:15]([O:19][C:20](=[O:25])[C@@H:21]([NH:24][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[N+:11]([O-:13])=[O:12])[CH2:22][CH3:23])([CH3:17])([CH3:16])[CH3:18]

参加物

8

反応物 4

HCID 172865-Chloro-2-nitrobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 53628861tert-Butyl (2S)-2-aminobutanoate--hydrogen chloride (1/1)

生成物 1

HCID 57725370HCID 57725370、化合物収率 85.7%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 111,2-Dichloroethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 5-chloro-2-nitro-benzoic acid (4.68 g) in anhydrous tetrahydrofuran (100 ml) at 0° C., was added (S)-2-amino-butyric acid-tert-butyl ester hydrochloric acid salt (5 g), HOBt (3.45 g), DMAP (2.98 g), followed by EDC (4.88 g) and diisopropylethylamine (3.30 g). The reaction mixture was stirred for 10 minutes then warmed to room temperature and stirred for 16 hours before concentration at reduced pressure. The resulting residue was partitioned between EtOAc (100 ml) and saturated sodium bicarbonate solution (100 ml), the organic layer separated and further washed with 1M hydrochloric acid and saturated brine solution, dried (MgSO4), filtered and concentrated to give the sub-title compound as a pale yellow oil (6.82 g, 68% yield). 1H NMR (400 MHz, CDCl3) δ 8.05 (1H, d), 7.55 (2H, m), 6.4 (1H, m) 4.7 (1H, m), 2.1 (1H, m), 1.95 (1H, m), 1.5 (9H, s), 1.0 (3H, t) ppm.

後処理

  1. stirringstirred for 16 hours before concentration at reduced pressure
  2. customThe resulting residue was partitioned between EtOAc (100 ml) and saturated sodium bicarbonate solution (100 ml)
  3. customthe organic layer separated
  4. washfurther washed with 1M hydrochloric acid and saturated brine solution
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-e9c92621a5524a60a88a69962a498714
出典データセット
uspto-grants-2012_03
特許番号
US08129381B2

反応ノート

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