Triethylamine → 5-phenylpentyl-N-methyl-N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]-carbamate

HRID 530532노트

반응식

HRID 530532 반응식
O[C@@H:2]([CH3:23])[C@@H:3]([N:7]([CH3:22])[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:9])[C:4]([OH:6])=[O:5].CCN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[C:16]1([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][O:10][C:8](=[O:9])[N:7]([CH3:22])[C@H:3]2[C:4](=[O:6])[O:5][C@H:2]2[CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 73294311(2R,3S)-3-hydroxy-2-[methyl-(5-phenylpentoxycarbonyl)-amino]-butanoic acid

생성물 1

HCID 732943125-phenylpentyl-N-methyl-N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]-carbamate수율 23.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a stirred mixture of (2R,3S)-3-hydroxy-2-[methyl-(5-phenylpentoxycarbonyl)-amino]-butanoic acid (0.04 g, 0.14 mmol) in dry CH2Cl2(5.0 mL), under nitrogen atmosphere at 0° C., Et3N (0.06 mL, 0.41 mmol) and subsequently TBTU (0.05 g, 0.17 mmol) were added. The mixture was left stirring at 0° C. for 1 h and at rt for 15 h. Upon full conversion of the starting material, the organics were removed under reduced pressure, and the resulting crude product absorbed over silica gel and purified by column chromatography, eluting with Cy:EtOAc (from 100:0 to 0:100) to afford the title compound (0.01 g, 23%), as a mixture of two rotamers (1:1.5 ratio), as a colorless oil. [α]25D −16.66 (c 0.1, CHCl3). 1H NMR (DMSO-d6) δ 1.29-1.41 (m, 10H), 1.53-1.69 (m, 8H), 2.58 (t, J=7.6 Hz, 4H), 2.93 (s, 6H), 3.98-4.11 (m, 4H), 4.77-4.89 (m, 2H), 5.24-5.33 (m, 1H, major rotamer), 5.35-5.43 (m, 1H, minor rotamer), 7.13-7.32 (m, 10H).

후처리

  1. waitThe mixture was left
  2. customUpon full conversion of the starting material, the organics were removed under reduced pressure
  3. customthe resulting crude product absorbed over silica gel
  4. custompurified by column chromatography
  5. washeluting with Cy

출처 및 근거

ORD 기록
ord-884e41c8730540169c11338bb228b64b
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353075B2

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