Formaldehyde → 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[N-(4-cyanophenylmethyl)-N-methylamino]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine

HRID 1829107ノート

反応式

HRID 1829107 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[C:23]([N:25]1[CH2:29][CH2:28][S:27][CH2:26]1)=[O:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.[C:32](C1C=CC(CN[C@@H]2CN[C@H](C(N3CCSC3)=O)C2)=CC=1)#N.C=O.C([BH3-])#N.[Na+]>C(#N)C.C(O)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)[CH3:32])[CH2:10][C@H:9]1[C:23]([N:25]1[CH2:29][CH2:28][S:27][CH2:26]1)=[O:24])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 4

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 675066143-[(2S,4S)-1-tert-Butoxycarbonyl-4-(4-cyanophenylmethyl)amino-2-pyrrolidinylcarbonyl]-1,3-thiazolidineHCID 675078123-[(2S,4S)-4-(4-cyanophenylmethyl)amino-2-pyrrolidinylcarbonyl]-1,3-thiazolidine dihydrochloride

生成物 1

HCID 675071013-{(2S,4S)-1-tert-butoxycarbonyl-4-[N-(4-cyanophenylmethyl)-N-methylamino]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒HCID 6342Acetonitrile溶媒

実験手順

3-[(2S,4S)-1-tert-Butoxycarbonyl-4-(4-cyanophenylmethyl)amino-2-pyrrolidinylcarbonyl]-1,3-thiazolidine [product of Example 63 (1), 1.35 g] and 37% formaldehyde solution (0.788 mL) were dissolved in acetonitrile (20 mL), and the mixture was stirred at room temperature for 30 min. Sodium cyanoborohydride (0.305 g) and several drops of acetic acid were added to the reaction mixture, and the reaction mixture was stirred for 1 hr. The reaction mixture was evaporated under reduced pressure. Saturated aqueous sodium hydrogencarbonate solution was added to the residue and the mixture was extracted with ethyl acetate. The extract was dried and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography to give 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[N-(4-cyanophenylmethyl)-N-methylamino]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine (0.953 g) as white amorphous.

後処理

  1. stirringthe reaction mixture was stirred for 1 hr
  2. customThe reaction mixture was evaporated under reduced pressure
  3. additionSaturated aqueous sodium hydrogencarbonate solution was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe extract was dried
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-63f9f6195f9746d39ec984762e2960c7
出典データセット
uspto-grants-2006_06
特許番号
US07060722B2

反応ノート

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