1,2-Dichloroethane → HCID 44600522, 화합물

HRID 882754노트

반응식

HRID 882754 반응식
[C:1]([N:8]1[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:9]1[C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[CH:18]1([N:22]2[CH2:28][CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH2:21][CH2:20][CH2:19]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>CN(C=O)C.C([O-])(O)=O.[Na+]>[C:4]([O:3][C:1]([N:8]1[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:9]1[C:10]([N:25]1[CH2:26][CH2:27][CH2:28][N:22]([CH:18]2[CH2:19][CH2:20][CH2:21]2)[CH2:23][CH2:24]1)=[O:12])=[O:2])([CH3:5])([CH3:6])[CH3:7]

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 88804(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acidHCID 69002457HCID 69002457, 화합물

생성물 1

HCID 44600522HCID 44600522, 화합물수율 56.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of N-Boc-trans-4-hydroxy-L-proline (1.0 g, 4.32 mmol), 1-cyclobutyl-[1,4]diazepane hydrochloride (981 mg, 4.32 mmol), EDC (869 mg, 4.54 mmol) and HOBt (583 mg, 4.32 mmol) in DMF (22 mL) was added Et3N (1.2 mL, 8.64 mmol). The solution was allowed to stir overnight at room temperature (rt). The mixture was diluted with 5% aqueous (aq.) NaHCO3 and extracted with CH2Cl2 (3×). The combined organic layers were dried and concentrated. Purification by FCC provided the desired product (897 mg, 56%). MS (ESI): mass calcd. for C19H33N3O4, 367.25; m/z found, 368.6 [M+H]+. 1H NMR (CDCl3): 4.81-4.67 (m, 1H), 4.59-4.48 (m, 1H), 3.79-3.42 (m, 6H), 2.92-2.80 (m, 1H), 2.63-2.30 (m, 4H), 2.26-2.07 (m, 2H), 2.07-1.97 (m, 3H), 1.91-1.75 (m, 4H), 1.73-1.54 (m, 2H), 1.48-1.39 (m, 9H).

후처리

  1. extractionextracted with CH2Cl2 (3×)
  2. customThe combined organic layers were dried
  3. concentrationconcentrated
  4. customPurification by FCC

출처 및 근거

ORD 기록
ord-de35d3d59a19417e8baad5682117db88
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236792B2

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