Diethylamine → HCID 10503756, 화합물

HRID 353438노트

반응식

HRID 353438 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([Br:24])[C:15]2[CH:20]=[CH:19][C:18]([C:21](O)=[O:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(Cl)=O)C(C)C.[CH2:33]([NH:35][CH2:36][CH3:37])[CH3:34]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([Br:24])[C:15]2[CH:16]=[CH:17][C:18]([C:21](=[O:22])[N:35]([CH2:36][CH3:37])[CH2:33][CH3:34])=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

5

반응물 3

HCID 8021DiethylamineHCID 62365Isobutyl chloroformateHCID 10834544HCID 10834544, 화합물

생성물 1

HCID 10503756HCID 10503756, 화합물수율 73%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of compound 5 (1.0 g, 2.5 mmol) in dry dichloromethane (10 mL) at −20° C. was added isobutylchloroformate (450 mg, 3.3 mmol). After 20 min at −20° C. diethylamine (4 mL) was added and the reaction was allowed to warm to room temperature. After 1.5 hrs the solvents were evaporated and the residue was partitioned between ethyl acetate and water. The organic phase was washed with brine and dried over MgSO4. Removal of solvents provided a crude product, which was purified by flash chromatography to give compound 6 as white needles (800 mg, 73%): IR (NaCl) 3051, 2975, 1694, 1633, 1416, 1281, 1168, 1115 cm−1; 1H NMR (CDCl3) δ1.13 (br, 3H), 1.22 (br, 3H), 1.44 (s, 9H),2.22 (t, J=5.5 Hz, 2H), 2.62 (t, J=5.5 Hz, 2H), 3.33 (m, 4H), 3.55 (m, 2H), 7.31 (d, J=8.0 Hz, 2H), 7.36 (d, J=8.0 Hz, 2H); 13C NMR (CDCl3) δ12.71, 14.13, 28.3, 31.5, 34.2, 39.1, 43.2, 79.7, 115.9, 126.3, 129.3, 136.8, 137.1, 140.6, 154.6, 170.

후처리

  1. customAfter 1.5 hrs the solvents were evaporated
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. customRemoval of solvents
  6. customprovided a crude product, which
  7. customwas purified by flash chromatography

출처 및 근거

ORD 기록
ord-6557d14af52344c5bbc22dc4abf27f52
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06753335B2

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