Acetic Acid → HCID 117601123, 화합물

HRID 578952노트

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HRID 578952 반응식
[F:1][C:2]1([F:16])[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][CH2:5][NH:4][CH2:3]1.[C:17]([BH3-])#N.[Na+].C=O.C(O)(=O)C>C1COCC1.C(OCC)(=O)C.CO>[F:16][C:2]1([F:1])[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH2:6][CH2:5][N:4]([CH3:17])[CH2:3]1

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 56924440tert-Butyl 6,6-difluoro-1,4-diazepane-1-carboxylate

생성물 1

HCID 117601123HCID 117601123, 화합물수율 98.6%

시약·촉매·용매 3

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
20 °C

실험 절차

Combined tert-butyl 6,6-difluoro-1,4-diazepane-1-carboxylate (49 mg, 0.207 mmol) and sodium cyanoborohydride (52 mg, 0.83 mmol) in THF (1.5 mL) and added 37% aqueous formaldehyde (0.077 mL, 1.037 mmol) and acetic acid (0.018 mL, 0.311 mmol) and then stirred at 20° C. for 16 h. Then methanol (300 uL) was added and the mixture was concentrated in vacuo to give a residue which was taken up in ethyl acetate (40 mL), washed with saturated aqueous sodium bicarbonate (50 mL) and brine, dried with magnesium sulfate and concentrated in vacuo to give the title compound (51 mg, 0.204 mmol, 98%) as a clear, colorless oil. MS: 251 (M+H). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.46 (s, 9 H) 2.50 (s, 3 H) 2.73 (d, J=4.8 Hz, 2 H) 2.92 (t, J=13.5 Hz, 2 H) 3.55 (d, J=4.8 Hz, 2 H) 3.75-3.94 (m, 2 H).

후처리

  1. concentrationthe mixture was concentrated in vacuo
  2. customto give a residue which
  3. washwashed with saturated aqueous sodium bicarbonate (50 mL) and brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-21de13718b3c4e13a831828d94616203
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040522B2

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