Methanol → HCID 52180852、化合物

HRID 1808791ノート

反応式

HRID 1808791 の反応式
[N:1]1([C:5](=[O:18])[C@@H:6]([NH:10]C(=O)OC(C)(C)C)[CH:7]([CH3:9])[CH3:8])[CH2:4][CH2:3][CH2:2]1.O1CCOCC1.CO>Cl>[NH2:10][C@@H:6]([CH:7]([CH3:9])[CH3:8])[C:5]([N:1]1[CH2:4][CH2:3][CH2:2]1)=[O:18]

参加物

5

反応物 3

HCID 887MethanolHCID 312751,4-Dioxane2 回HCID 52180842tert-Butyl [(2S)-1-(azetidin-1-yl)-3-methyl-1-oxobutan-2-yl]carbamate2 回

生成物 1

HCID 52180852HCID 52180852、化合物収率 73.2%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒2 回

実験手順

(S)-Tert-butyl 1-(azetidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (Compound D) (23.56 g, 90.07 mmol) was stirred in 4M HCl in dioxane (56.3 mL, 225 mmol) for 30 min. Additional dioxane and MeOH was added until the reaction mixture became a clear solution. The solvent was removed under reduced pressure and conc. HCl (3.00 mL, 30.4 mmol) was added. The mixture was stirred for 5 h before the solvent was removed. The residue was purified via Biotage (gradient; EtOAc:MeOH (2% TEA), 99:1 to 90:10, then EtOAc:MeOH (2% TEA) 90:10 to 0/100 KP-SIL 340 g. The solvent was removed under reduced pressure to give the title compound (10.3 g, 70.3%). 1H NMR (600 MHz, CH3OD) δ 1.03, 1.06, 2.07-2.16, 2.33-2.41, 3.71, 3.99-4.07, 4.07-4.14, 4.25-4.33, 4.33-4.41. Total no of protons: 14. LCMS (M+H)+: 157.

後処理

  1. additionwas added
  2. customwas removed
  3. customThe residue was purified via Biotage (gradient
  4. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-0e50734ca9494ec0b771495786ae106d
出典データセット
uspto-grants-2013_01
特許番号
US08361998B2

反応ノート

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