Methanol → HCID 52180852, 화합물

HRID 1808791노트

반응식

HRID 1808791 반응식
[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]

참가 물질

5

반응물 3

HCID 887MethanolHCID 312751,4-Dioxane2회HCID 52180842tert-Butyl [(2S)-1-(azetidin-1-yl)-3-methyl-1-oxobutan-2-yl]carbamate2회

생성물 1

HCID 52180852HCID 52180852, 화합물수율 73.2%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매2회

실험 절차

(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.

후처리

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

출처 및 근거

ORD 기록
ord-0e50734ca9494ec0b771495786ae106d
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08361998B2

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