Hydrochloric Acid → 2-Adamantyl 3-((tert-butoxycarbonylamino)methyl)azetidine-1-carboxylate

HRID 72126ノート

反応式

HRID 72126 の反応式
[NH:1]1[CH2:4][CH:3]([CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2]1.CCN(C(C)C)C(C)C.Cl[C:24]([O:26][CH:27]1[CH:34]2[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:36][CH:28]1[CH2:29]3)[CH2:33]2)=[O:25].C(Cl)Cl.Cl>>[C:9]([O:8][C:7]([NH:6][CH2:5][CH:3]1[CH2:4][N:1]([C:24]([O:26][CH:27]2[CH:28]3[CH2:36][CH:32]4[CH2:31][CH:30]([CH2:35][CH:34]2[CH2:33]4)[CH2:29]3)=[O:25])[CH2:2]1)=[O:13])([CH3:10])([CH3:12])[CH3:11]

参加物

6

反応物 5

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 108785372-adamantyl ChloroformateHCID 15346872tert-butyl N-(azetidin-3-ylmethyl)carbamate

生成物 1

HCID 444733662-Adamantyl 3-((tert-butoxycarbonylamino)methyl)azetidine-1-carboxylate収率 23%

実験手順

A vial was charged with tert-butyl azetidin-3-ylmethylcarbamate (25 mg, 0.12 mmol), i-Pr2NEt (31 μL, 0.17 mmol) and a flea stir bar. A solution of 2-adamantyl chloroformate in CH2Cl2 (1.5 mL, 17 mg mL−1, 0.12 mmol) was added. The mixture was stirred overnight at rt. A 10-mL ChemElut cartridge (Varian Inc. catalog number 12198007) was wetted with 5% aq HCl (5 mL) and allowed to stand for 5 min. The reaction mixture was applied to the cartridge and eluted with ether (20 mL). The eluate was evaporated to dryness and the residue was purified by preparative HPLC to afford the title compound (10 mg, 23%). 1H NMR (CDCl3) δ 1.42 (s, 9H), 1.5-2.0 (14H), 2.76 (m, 1H), 3.35 (m, 2H), 3.67 (m, 2H), 4.03 (m, 2H), 4.68 (m, 1H), 4.78 (s, 1H); LC-MS Method 1 tR=2.08 min, m/z=387, 365, 309.

後処理

  1. stirringThe mixture was stirred overnight at rt
  2. washeluted with ether (20 mL)
  3. customThe eluate was evaporated to dryness
  4. customthe residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-2d93cf5715574d9f865ec399ec289624
出典データセット
uspto-grants-2014_09
特許番号
US08828985B2

反応ノート

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