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

HRID 1783425ノート

反応式

HRID 1783425 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-bd3714c40d89410691f4cfe1b050b370
出典データセット
uspto-grants-2009_03
特許番号
US07501404B2

反応ノート

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