Phenylacetic Acid → tert-butyl (2S)-2-[(Z)-N'-(2-phenylacetyl)oxycarbamimidoyl]piperidine-1-carboxylate

HRID 397645ノート

反応式

HRID 397645 の反応式
O.ON1C2C=CC=CC=2N=N1.[C:12]1([CH2:18][C:19]([OH:21])=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC.[NH2:41]/[C:42](=[N:56]\O)/[C@@H:43]1[CH2:48][CH2:47][CH2:46][CH2:45][N:44]1[C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50]>CN(C)C1C=CN=CC=1.ClCCl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[NH2:56]/[C:42](=[N:41]\[O:20][C:19](=[O:21])[CH2:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)/[C@@H:43]1[CH2:48][CH2:47][CH2:46][CH2:45][N:44]1[C:49]([O:51][C:52]([CH3:54])([CH3:53])[CH3:55])=[O:50]

参加物

9

反応物 5

HCID 999Phenylacetic AcidHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59085902tert-butyl (2S)-2-[(Z)-N'-hydroxycarbamimidoyl]piperidine-1-carboxylate

生成物 1

HCID 59085894tert-butyl (2S)-2-[(Z)-N'-(2-phenylacetyl)oxycarbamimidoyl]piperidine-1-carboxylate収率 91.3%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 311Citric Acid溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

1-Hydroxybenzotriazole hydrate (8.67 g), phenylacetic acid (8.0 g), N-methylmorpholine (14.69 ml), 4-dimethylaminopyridine (3.3 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (12.29 g) were added to a solution of tert-butyl (Z)-(2S)-2-[amino(hydroxyimino)methyl]-1-piperidinecarboxylate (13.0 g) [see Preparation 4] in dichloromethane (180 ml). The reaction mixture was stirred for 2 hours under an atmosphere of nitrogen, after which time the mixture was diluted with dichloromethane and 1N aqueous citric acid solution. The organic layer was separated, washed with saturated aqueous sodium hydrogen carbonate solution, dried over magnesium sulphate and the solvent was removed under reduced pressure to afford tert-butyl (Z)-(2S)-2-(amino[(2-phenylacetyl)oxy]iminomethyl)-1-piperidinecarboxylate (17.63 g) as a white solid.

後処理

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over magnesium sulphate
  4. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-cec9c0ea11454573afd45b9294fbc604
出典データセット
uspto-grants-2003_08
特許番号
US06610707B1

反応ノート

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