Pivaloyl chloride → N-(4,5-Difluoro-2-(hydroxymethyl)phenyl)pivalamide

HRID 1985528ノート

反応式

HRID 1985528 の反応式
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].[NH2:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[CH:11][C:10]=1[CH2:17][OH:18].CCN(C(C)C)C(C)C>C(Cl)Cl.C1COCC1>[F:16][C:12]1[C:13]([F:15])=[CH:14][C:9]([NH:8][C:3](=[O:4])[C:2]([CH3:7])([CH3:6])[CH3:1])=[C:10]([CH2:17][OH:18])[CH:11]=1

参加物

5

反応物 3

HCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 21925570(2-Amino-4,5-difluorophenyl)methanol

生成物 1

HCID 59732039N-(4,5-Difluoro-2-(hydroxymethyl)phenyl)pivalamide

試薬・触媒・溶媒 1

HCID 21919333Tetrahydrofurane dichloromethane溶媒

実験手順

Trimethylacetyl chloride (4.01 mL, 32.55 mmol) was added to the solution of the crude (2-amino-4,5-difluorophenyl)methanol in CH2Cl2/THF (50 mL/10 mL) at 0° C., followed by the addition of DIEA (10.8 mL, 62 mmol). The resulting mixture was stirred for 30 min, and then partitioned between saturated NaHCO3 (100 mL) and CH2Cl2 (150 mL). After separation, the organic phase was washed with brine (40 mL), dried over MgSO4, and concentrated on rotary vacuum to afford the expected product, which was pure enough to be used in next step without further purification; 1H NMR (400 MHz, CDCl3) δ ppm 1.28 (s, 9H), 4.62 (s, 2H), 6.94 (dd, J=10.20, 8.44 Hz, 1H), 8.08 (dd, J=12.72, 7.68 Hz, 1H), 9.04 (s, 1H); Mass spec. 244.11 (MH+), Calc. for C12H15F2NO2 243.11.

後処理

  1. custompartitioned between saturated NaHCO3 (100 mL) and CH2Cl2 (150 mL)
  2. customAfter separation
  3. washthe organic phase was washed with brine (40 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated on rotary vacuum

出典と根拠

ORDレコード
ord-215d7698488e453789f2e92ca6d19d0d
出典データセット
uspto-grants-2009_06
特許番号
US07544680B2

反応ノート

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