Ammonia → (1S,3R)-benzyl 3-acetamido-2,2-dimethylcyclobutanecarboxylate

HRID 2179727ノート

反応式

HRID 2179727 の反応式
C([C@@H:4]1[CH2:7][C@H:6]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[C:5]1([CH3:19])[CH3:18])(=O)C.[N-]=[N+]=[N-].[Na+].CS(O)(=O)=O.[NH3:29].[CH2:30]([CH2:33]OC)[O:31]C>>[C:30]([NH:29][C@@H:4]1[CH2:7][C@H:6]([C:8]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:9])[C:5]1([CH3:18])[CH3:19])(=[O:31])[CH3:33]

参加物

6

反応物 5

HCID 222AmmoniaHCID 6395Methanesulfonic AcidHCID 80711,2-DimethoxyethaneHCID 33557Sodium AzideHCID 58111012(1S,3R)-benzyl 3-acetyl-2,2-dimethylcyclobutanecarboxylate

生成物 1

HCID 86650107(1S,3R)-benzyl 3-acetamido-2,2-dimethylcyclobutanecarboxylate収率 82.2%

実験手順

A stirred solution of (1S,3R)-benzyl 3-acetyl-2,2-dimethylcyclobutanecarboxylate (1.5 g, 5.76 mmol) in monoglyme (18.75 ml) at −45° C., NaN3 (1.12 g, 17.30 mmol), MeSO3H (10.5 ml), were added drop wise slowly and the reaction was allowed to stir at room temperature for about 48 hours. After completion of the reaction (monitored by TLC), the reaction mixture was neutralized with aqueous ammonia solution. Solvent was evaporated and diluted with DCM. Organic layer was washed with water, brine dried over Na2SO4. The solvent was evaporated under reduced pressure and the resulting crude purified by silica gel column (60/120 mesh, elution: 30% EtOAc in Hexane) to afford the title compound as off white solid. Wt: 1.3 g; Yield: 82.2%; 1H NMR (300 MHZ, CD3OD): δ 7.42-7.31 (m, 5H), 5.59 (d, 1H, J=5.7 Hz), 5.12 (s, 2H), 4.13 (q, 1H, J=9.3 Hz), 2.69-2.63 (m, 1H), 2.38-2.34 (m, 1H), 2.13-2.06 (m, 1H), 2.05 (s, 3H), 1.30 (s, 3H), 0.86 (s, 3H). Mass: [M+1]+ 276 (100%), [M+Na]+ 298 (66%); IR (KBr, cm−1): 3270, 2963, 2866, 1728, 1647, 1571, 1455, 1303, 1151, 1071, 1019, 961, 755, 742; M.R: 85.6° C.-97.5° C.

後処理

  1. customAfter completion of the reaction (monitored by TLC)
  2. customSolvent was evaporated
  3. additiondiluted with DCM
  4. washOrganic layer was washed with water, brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated under reduced pressure
  7. customthe resulting crude purified by silica gel column (60/120 mesh, elution: 30% EtOAc in Hexane)

出典と根拠

ORDレコード
ord-7784a036fad24a98a232ad1c7909d280
出典データセット
uspto-grants-2015_06
特許番号
US09067966B2

反応ノート

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