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

HRID 72126노트

반응식

HRID 72126 반응식
[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]

참가 물질

6

반응물 5

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2d93cf5715574d9f865ec399ec289624
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828985B2

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