5-Chloro-2-nitrobenzoic acid → HCID 57725370, 화합물

HRID 1091433노트

반응식

HRID 1091433 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

HCID 57725370HCID 57725370, 화합물수율 85.7%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 111,2-Dichloroethane용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e9c92621a5524a60a88a69962a498714
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129381B2

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