4-Methylmorpholine → HCID 67772960, 화합물

HRID 1808773노트

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HRID 1808773 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH:13]1[CH2:15][CH2:14]1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N:17]1[CH2:22][CH2:21]OC[CH2:18]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.N1CCC1>CN(C=O)C>[N:17]1([C:10](=[O:12])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH:13]2[CH2:15][CH2:14]2)[CH2:18][CH2:21][CH2:22]1

참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 10422AzetidineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2761461{[tert-Butoxy(hydroxy)methylidene]amino}(cyclopropyl)acetic acid

생성물 1

HCID 67772960HCID 67772960, 화합물수율 86.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

(S)-2-(Tert-butoxycarbonylamino)-2-cyclopropylacetic acid (2.0 g, 9.30 mmol), which is commercially available, and NMM (3.07 mL, 27.9 mmol) was mixed in DMF (20 mL). The mixture was cooled to 0° C. and TBTU (3.34 g, 10.42 mmol) was added. After 10 min at rt was azetidine (1.6 mL, 23.7 mmol) added. The resultant mixture was stirred at rt over night. The mixture was concentrated and the residue dissolved in DCM (300 mL). The organic phase was washed with NaHCO3 (saturated, 150 mL) and brine (150 mL), filtered through a phase separator and concentrated under reduced pressure to give the title compound (2.04 g, 86%). The obtained crude product was used without further purification. 1H NMR (400 MHz, CD3OD) δ 0.39, 0.44-0.63, 1.09, 1.43, 2.31, 3.84, 3.93-4.46, 5.30. Total no of protons: 22.

후처리

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue dissolved in DCM (300 mL)
  3. washThe organic phase was washed with NaHCO3 (saturated, 150 mL) and brine (150 mL)
  4. filtrationfiltered through a phase separator
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e3d47ccf14b54bc386b17e3b9ea6c267
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08361998B2

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