Dicyclohexylcarbodiimide → HCID 688299, 화합물

HRID 1874644노트

반응식

HRID 1874644 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@@H:9]1[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.[CH3:51][NH:52][O:53][CH3:54]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:54][O:53][N:52]([CH3:51])[C:10]([C@H:9]1[CH2:13][CH2:14][CH2:15][N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:12]

참가 물질

8

반응물 5

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 688022(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid

생성물 1

HCID 688299HCID 688299, 화합물수율 48.4%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

N-(tert-Butoxycarbonyl)-D-proline (1.505 g, 6.99 mmol), DCC (1.443 g, 6.99 mmol), HOBt (1.071 g, 6.99 mmol), and Hunig's base (2.78 mL, 15.89 mmol) in DCM (31.8 mL) were stirred at room temperature for 1 h. N,O-Dimethylhydroxylamine hydrochloride (0.62 g, 6.36 mmol) and DMAP (0.078 g, 0.636 mmol) were added and the solution stirred at room temperature for 4 h. The mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel (10%→100% ethyl acetate in hexanes). Obtained (R)-tert-butyl 2-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate (794 mg, 3.07 mmol, 48.4% yield) as a colorless oil. Rotomers (a and b) seen in NMR: 1H NMR (500 MHz, CDCl3) δ 4.52-4.76 (m, 1H), 3.77 (s, 1.5 Ha), 3.71 (s, 1.5 Hb), 3.51-3.64 (m, 1H), 3.33-3.51 (m, 1H), 3.18 (s, 3H), 2.08-2.27 (m, 1H), 1.74-2.04 (m, 3H), 1.45 (s, 4.5 Ha), 1.40 (s, 4.5 Hb); LRMS (ESI) m/e 158.76.

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was purified by column chromatography on silica gel (10%→100% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-52496683a94c473c874510fec472ddb8
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304577B2

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