4-Methoxybenzyl alcohol → (2S,3R)-3-Allyl-1-(tert-butyl-dimethyl-silanyl)-4-oxo-azetidine-2-carboxylic acid 4-methoxy-benzyl ester

HRID 1783425노트

반응식

HRID 1783425 반응식
[CH2:1]([C@H:4]1[C:7](=[O:8])[N:6]([Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[C@@H:5]1[C:16]([OH:18])=[O:17])[CH:2]=[CH2:3].CCN=C=NCCCN(C)C.Cl.[CH3:31][O:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37]O)=[CH:35][CH:34]=1>CN(C1C=CN=CC=1)C.ClCCl>[CH3:31][O:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37][O:17][C:16]([C@@H:5]2[C@@H:4]([CH2:1][CH:2]=[CH2:3])[C:7](=[O:8])[N:6]2[Si:9]([C:12]([CH3:13])([CH3:14])[CH3:15])([CH3:10])[CH3:11])=[O:18])=[CH:35][CH:34]=1

참가 물질

6

반응물 3

HCID 77384-Methoxybenzyl alcoholHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14586689(2S,3R)-3-Allyl-1-(tert-butyl-dimethyl-silanyl)-4-oxo-azetidine-2-carboxylic acid

생성물 1

HCID 57589741(2S,3R)-3-Allyl-1-(tert-butyl-dimethyl-silanyl)-4-oxo-azetidine-2-carboxylic acid 4-methoxy-benzyl ester수율 49%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

A mixture of 900 mg of crude compound 57 (3.34 mmol) above, EDC hydrochloride salt (1.34 g, 7.01 mmol), DMAP (83 mg, 0.67 mmol) and 4-methoxybenzyl alcohol (1.40 g, 10.1 mmol) in dichloromethane (9 mL) was stirred at room temperature overnight. The solvent was removed in vacuo. The residue was dissolved with ethyl acetate, washed with 5% aqueous KHSO4, water (×2) and brine (×1). The organic layer was dried over Na2SO4, then concentrated to yield the crude 58 with LC purity: 60%. Purification by ISCO silica gel column using 0-20% AcOEt in Hexanes afforded 630 mg of compound 58 (49% yield, 81% purity): 1HNMR (300 MHz, CDCl3): 0.13 (s, 3H), 0.32 (s, 3H), 0.95 (s, 9H), 2.56 (m, 2H), 3.43 (m, 1H), 3.81 (d, J=2.60 Hz, 1H), 3.82 (s, 3H), 4.67 (s, 2H), 5.17 (m, 2H), 5.72 (m, 1H), 6.94 (d, 2H), 7.34 (d, 2H). Anal. C21H31NO4Si, Mol. Wt.: 389.56. Found: ESI-MS: 390.0 (M+H)+.

후처리

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved with ethyl acetate
  3. washwashed with 5% aqueous KHSO4, water (×2) and brine (×1)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customto yield the crude 58 with LC purity: 60%
  7. customPurification by ISCO silica gel column

출처 및 근거

ORD 기록
ord-bd3714c40d89410691f4cfe1b050b370
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07501404B2

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