2-Bromopropane → HCID 57968657, 화합물

HRID 882759노트

반응식

HRID 882759 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14]([N:16]1[CH2:22][CH2:21][CH2:20][N:19]([CH:23]2[CH2:26][CH2:25][CH2:24]2)[CH2:18][CH2:17]1)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH:30]([CH3:32])[CH3:31]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][CH:30]([CH3:32])[CH3:31])[CH2:10][C@H:9]1[C:14]([N:16]1[CH2:22][CH2:21][CH2:20][N:19]([CH:23]2[CH2:24][CH2:25][CH2:26]2)[CH2:18][CH2:17]1)=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 44600522HCID 44600522, 화합물

생성물 1

HCID 57968657HCID 57968657, 화합물수율 8.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of (2S,4R)-2-(4-cyclobutyl-[1,4]diazepane-1-carbonyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (287 mg, 0.78 mmol) in DMF (7.8 mL) was added NaH (90%; 31 mg). After 30 min, 2-bromopropane (109 μL, 1.17 mmol) was added and the mixture was allowed to warm to rt and was stirred for 18 h. The mixture was diluted with satd. aq. NaHCO3 and extracted with CH2Cl2. The combined organic layers were dried and concentrated. The crude product was purified by FCC to provide the desired product (26 mg, 8%). MS (ESI): mass calcd. for C22H39N3O4, 409.29; m/z found, 410.4 [M+H]+. 1H NMR (CDCl3): 4.74-4.58 (m, 1H), 4.33-4.16 (m, 1H), 3.74-3.33 (m, 7H), 2.90-2.78 (m, 1H), 2.59-2.30 (m, 4H), 2.19-2.11 (m, 1H), 2.10-1.96 (m, 4H), 1.87-1.72 (m, 3H), 1.69-1.53 (m, 2H), 1.40 (d, J=17.6 Hz, 9H), 1.12 (dd, J=6.0, 2.2 Hz, 6H).

후처리

  1. additionThe mixture was diluted with satd
  2. extractionaq. NaHCO3 and extracted with CH2Cl2
  3. customThe combined organic layers were dried
  4. concentrationconcentrated
  5. customThe crude product was purified by FCC

출처 및 근거

ORD 기록
ord-5e9dcf26c7184798b5266fdf197e4dec
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236792B2

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