9-Fluorenylmethyl chloroformate → 3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2,2-dimethylpropanoic acid

HRID 74763

反応式

HRID 74763 の反応式
Cl.[NH2:2][CH2:3][C:4]([CH3:9])([CH3:8])[C:5]([OH:7])=[O:6].C(N(C(C)C)CC)(C)C.[CH:19]1[C:31]2[CH:30]([CH2:32][O:33][C:34](Cl)=[O:35])[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]=2[CH:22]=[CH:21][CH:20]=1>ClCCl>[CH:19]1[C:31]2[CH:30]([CH2:32][O:33][C:34]([NH:2][CH2:3][C:4]([CH3:9])([CH3:8])[C:5]([OH:7])=[O:6])=[O:35])[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]=2[CH:22]=[CH:21][CH:20]=1

参加物

5

反応物 3

HCID 343679-Fluorenylmethyl chloroformateHCID 81531DiisopropylethylamineHCID 534077243-Amino-2,2-dimethylpropanoic acid hydrochloride

生成物 1

HCID 450244313-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2,2-dimethylpropanoic acid収率 45.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To 3-amino-2,2-dimethylpropanoic acid, hydrochloride salt (250 mg, 1.63 mmol, 1 eq.) in dichloromethane (4 mL, 0.4 M) was added diisopropylethylamine (859 μL, 4.88 mmol, 3 eq.) followed by (9H-fluoren-9-ylmethoxy)carbonyl chloride (473 mg, 1.79 mmol, 1.1 eq.) The reaction was stirred for 18 hours and then concentrated in vacuo. The residue was taken up in ethyl acetate (3 mL) and washed with 1 M aqueous hydrochloric acid solution (2×1 mL) and with brine. The organic layer was dried over sodium sulfate, filtered, and purified by silica gel chromatography (Gradient: 0% to 100% ethyl acetate in heptane) to give #93 (250 mg, 45%) as an oil. 1H NMR (400 MHz, DMSO-d6) δ 12.22 (s, 1H), 7.89 (d, J=7.4 Hz, 2H), 7.72 (d, J=7.4 Hz, 2H), 7.38-7.44 (m, 2H), 7.27-7.35 (m, 3H), 4.18-4.30 (m, 3H), 3.16 (d, J=6.2 Hz, 2H), 1.05 (s, 6H).

後処理

  1. concentrationconcentrated in vacuo
  2. washwashed with 1 M aqueous hydrochloric acid solution (2×1 mL) and with brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. custompurified by silica gel chromatography (Gradient: 0% to 100% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-e69ad027905349daab7a1ad374bc14e2
出典データセット
uspto-grants-2014_09
特許番号
US08828401B2

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