4-Methylmorpholine → HCID 67772960、化合物

HRID 1808773ノート

反応式

HRID 1808773 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 67772960HCID 67772960、化合物収率 86.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-e3d47ccf14b54bc386b17e3b9ea6c267
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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