Triphenylphosphine → (R)-4-((R)-1-(5-(benzyloxy)benzo[d]thiazol-7-yloxy)ethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one

HRID 2209178노트

반응식

HRID 2209178 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([OH:18])[C:12]2[S:16][CH:15]=[N:14][C:13]=2[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[C@H:20]([C@H:22]1[CH2:26][N:25]([C@@H:27]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[CH3:28])[C:24](=[O:37])[CH2:23]1)[CH3:21].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([O:18][C@@H:20]([C@H:22]2[CH2:26][N:25]([C@@H:27]([C:29]3[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=3)[CH3:28])[C:24](=[O:37])[CH2:23]2)[CH3:21])[C:12]2[S:16][CH:15]=[N:14][C:13]=2[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 11776Triphenylphosphine2회HCID 5462977Diethyl azodicarboxylate2회HCID 71238294(4R)-4-[(1S)-1-hydroxyethyl]-1-[(1R)-1-(4-methoxyphenyl)ethyl]pyrrolidin-2-one2회HCID 1178430995-(Benzyloxy)benzo[d]thiazol-7-ol

생성물 1

HCID 117843340(R)-4-((R)-1-(5-(benzyloxy)benzo[d]thiazol-7-yloxy)ethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
40 °C

실험 절차

5-(benzyloxy)benzo[d]thiazol-7-ol (420 mg, 1.63 mmol), (R)-4-((S)-1-hydroxyethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one (607 mg, 2.31 mmol), and PPh3 (615 mg, 2.35 mmol) were dissolved in THF (15 ml). DEAD (0.36 mL, 2.30 mmol) was added and the resulting mixture was heated to 40° C. After 17 h, additional (R)-4-((S)-1-hydroxyethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one (105 mg, 0.40 mmol), PPh3 (110 mg, 0.42 mmol) and DEAD (0.060 mL, 0.38 mmol) were added. The reaction mixture was stirred an additional 1.5 h and was then concentrated directly onto silica gel. Purification by silica gel chromatography (70 to 100% EtOAc in hexanes) provided (R)-4-((R)-1-(5-(benzyloxy)benzo[d]thiazol-7-yloxy)ethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one 4.03C. LCMS-ESI+ (m/z): [M+H]+ calcd for C29H31N2O4S: 503.2; found 503.2.

후처리

  1. concentrationwas then concentrated directly onto silica gel
  2. customPurification by silica gel chromatography (70 to 100% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-32298a45a32a495880c1c2ee9660b84f
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376441B2

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