4-Methylmorpholine → N-[[1,2,3,4-Tetrahydro-2-[(acetylthio)methyl]-2-naphthalenyl]carbonyl]-isoserine, benzyl ester

HRID 1656056ノート

反応式

HRID 1656056 の反応式
[C:1]([C:4]1([CH2:14][S:15][C:16](=[O:18])[CH3:17])[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)([OH:3])=O.CN1CCOCC1.S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH2:37]([O:44][C:45](=[O:50])[CH:46]([OH:49])[CH2:47][NH2:48])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[C:16]([S:15][CH2:14][C:4]1([C:1]([NH:48][CH2:47][CH:46]([C:45]([O:44][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:50])[OH:49])=[O:3])[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)(=[O:18])[CH3:17]

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 197899352-Carboxy-2-[(acetylthio)methyl]-1,2,3,4-tetrahydronaphthaleneHCID 88125266Isoserine benzyl ester tosylate salt

生成物 1

HCID 88127936N-[[1,2,3,4-Tetrahydro-2-[(acetylthio)methyl]-2-naphthalenyl]carbonyl]-isoserine, benzyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Dissolve 2-carboxy-2-[(acetylthio)methyl]-1,2,3,4-tetrahydronaphthalene (2.88 g, 10.0 mmol) in dry dimethylformamide (20 mL). To this solution add N-methyl morpholine (1.01 g, 10.0 mmol), isoserine benzyl ester tosylate salt (3.67 g, 10.0 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.92 g, 10.0 mmol). Stir the reaction mixture for 18 hours under an atmosphere of argon at ambient temperature then partition between ethyl acetate and dilute HCl. Wash the organic solution with water, saturated sodium hydrogen carbonate then brine. Dry the solution (MgSO4) and concentrate in vacuo. Purify the residue by column chromatography (ethyl acetate:hexane) to give the title compound.

後処理

  1. customthen partition between ethyl acetate and dilute HCl
  2. washWash the organic solution with water, saturated sodium hydrogen carbonate
  3. dry with materialDry the solution (MgSO4)
  4. concentrationconcentrate in vacuo
  5. customPurify the residue by column chromatography (ethyl acetate:hexane)

出典と根拠

ORDレコード
ord-abd1491b6eac43038c4de47262fb2b6e
出典データセット
uspto-grants-1993_10
特許番号
US05252601

反応ノート

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