Potassium Carbonate → HCID 86654423、化合物

HRID 2067855ノート

反応式

HRID 2067855 の反応式
C([O:4][C:5]1([C@:9]2([C:29]([N:31]3[CH2:36][C@@H:35]4[CH2:37][C@H:32]3[CH2:33][N:34]4[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[O:30])[CH2:13][CH2:12][C@@H:11]([N:14]([C:23](=[O:28])[C:24]([F:27])([F:26])[F:25])[C@@H:15]3[C@H:20]([O:21][CH3:22])[CH2:19][O:18][CH2:17][CH2:16]3)[CH2:10]2)[CH2:8][CH2:7][CH2:6]1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[C:41]([O:40][C:38]([N:34]1[CH2:33][C@@H:32]2[CH2:37][C@H:35]1[CH2:36][N:31]2[C:29]([C@@:9]1([C:5]2([OH:4])[CH2:6][CH2:7][CH2:8]2)[CH2:13][CH2:12][C@@H:11]([N:14]([C:23](=[O:28])[C:24]([F:26])([F:27])[F:25])[C@@H:15]2[C@H:20]([O:21][CH3:22])[CH2:19][O:18][CH2:17][CH2:16]2)[CH2:10]1)=[O:30])=[O:39])([CH3:44])([CH3:42])[CH3:43]

参加物

4

反応物 2

HCID 11430Potassium CarbonateHCID 86654424HCID 86654424、化合物

生成物 1

HCID 86654423HCID 86654423、化合物収率 100%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 1.43 g (2.26 mmol) of 3-{[(1R,3S)-3-[1-(acetyloxy)cyclobutyl]-3-{[(1S,4S)-5-(tert-butoxycarbonyl)-2,5-diazabicyclo[2.2.1]hept-2-yl]carbonyl}cyclopentyl](trifluoroacetyl)amino}-1,5-anhydro-2,3-dideoxy-4-O-methyl-D-erythro-pentitol and 1.60 g (11.6 mmol) of powdered potassium carbonate in 8 mL of methanol was stirred at ambient temperature for 18 h, then partitioned between dichloromethane and brine, with sufficient water to dissolve solids. The organic phase was dried (Na2SO4) and concentrated under reduced pressure. Flash chromatography of the residue on silica using acetate to provide 1.33 g (100%) of the title compound as a white foam. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.34-1.62 (m, 10H) 1.66-2.93 (m, 15H) 3.20-3.63 (m, 8H) 3.66-4.03 (m, 3H) 4.06-4.24 (m, 3H) 4.25-4.65 (m, 2H) 4.68-5.29 (m, 1H). TLC Rf 0.33 (EtOAc). LC-MS ES+ 590.3.

後処理

  1. custompartitioned between dichloromethane and brine, with sufficient water
  2. dissolutionto dissolve solids
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-f33aa79fc1a8464592835e847042bc52
出典データセット
uspto-grants-2012_10
特許番号
US08293903B2

反応ノート

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