Triethylamine → Carbamic acid, [2-[hexahydro-4-(3-phenylpropyl)-1H-1,4-diazepin-1-yl]-2-oxoethyl]-, 1,1-dimethylethyl ester

HRID 1978375ノート

反応式

HRID 1978375 の反応式
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.Cl.Cl.[C:38]1([CH2:44][CH2:45][CH2:46][N:47]2[CH2:53][CH2:52][CH2:51][NH:50][CH2:49][CH2:48]2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C1CCN2C(=NCCC2)CC1.C(N(CC)CC)C>C(#N)C>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([N:50]1[CH2:51][CH2:52][CH2:53][N:47]([CH2:46][CH2:45][CH2:44][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:48][CH2:49]1)=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

8

反応物 6

HCID 8471TriethylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 219936901-(3-Phenylpropyl)-1,4-diazepane dihydrochloride

生成物 1

HCID 53890841Carbamic acid, [2-[hexahydro-4-(3-phenylpropyl)-1H-1,4-diazepin-1-yl]-2-oxoethyl]-, 1,1-dimethylethyl ester

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a suspension of 2.8 g (15.98 mmol.) of N-tert-butoxycarbonyl glycine and 3.67 g (23.96 mmol.) of 1-hydroxybenzotriazole monohydrate was added, at room temperature, 4.6 g (24.0 mmol.) of N-ethyl-N′-3-(N,N-dimethylamino)propylcarbodiimide hydrochloride. The mixture was stirred for one hour. To the reaction system, was added an acetonitrile solution (20 ml) of 5.65 (16.99 mmol.) of 1-(3-phenylpropan-1-yl)-2,3,5,6-tetrahydro-7H-1,4-diazepine dihydrochloride, 5.17 g (33.96 mmol.) of 1,8-diazabicyclo[5.4.0]unde-7-cene (DBU) and 2.3 ml (16.5 mmol.) of triethylamine. The mixture was stirred for 2 hours. The solvent was distilled off under reduced pressure. To the residue was added water, which was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous saline solution, which was dried over magnesium sulfate, followed by distilling off the solvent under reduced pressure. The crude product thus-obtained was purified by means of a column chromatography (methanol/ethyl acetate 10-20%). The solvent was distilled off under reduced pressure to afford the object compound as a pale yellow oily product. The yield was 5.64 g (94%).

後処理

  1. additionwas added, at room temperature
  2. stirringThe mixture was stirred for 2 hours
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionTo the residue was added water, which
  5. extractionwas subjected to extraction with ethyl acetate
  6. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate
  7. dry with materiala saturated aqueous saline solution, which was dried over magnesium sulfate
  8. distillationby distilling off the solvent under reduced pressure

出典と根拠

ORDレコード
ord-e02e7f5a006d44ed90cf36b810399b29
出典データセット
uspto-grants-2001_05
特許番号
US06235731B1

反応ノート

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