Hydrochloric Acid → Methyl alpha-amino-p-methoxycarbonylmethylphenylacetate

HRID 1289239ノート

反応式

HRID 1289239 の反応式
C(OC([NH:8][CH:9]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:16][CH:15]=1)[C:10]([O:12][CH3:13])=[O:11])=O)(C)(C)C.C(O)(C(F)(F)F)=O.Cl>C(Cl)Cl.CCOCC.CO.CCOCC>[NH2:8][CH:9]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:16][CH:15]=1)[C:10]([O:12][CH3:13])=[O:11]

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 54316225Methyl alpha-tert-butoxycarbonylamino-p-methoxycarbonylmethyl-phenylacetate

生成物 1

HCID 54294376Methyl alpha-amino-p-methoxycarbonylmethylphenylacetate

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒HCID 21864698Diethyl ether methanol溶媒

実験手順

To a solution of methyl α-tert-butoxycarbonylamino-p-methoxycarbonylmethyl-phenylacetate (2.86 g, 8.5 mmol) in CH2Cl2 (10 ml) cooled at 0° C. was added 10 ml of TFA. After stirring for 1 hour at room temperature the reaction mixture was evaporated to dryness. The resulting solid was dissolved in ethyl acetate and water and the pH was adjusted to 8 with NaHCO3. After extraction with ethyl acetate the organic layers were washed with brine, dried and evaporated to give a yellow oil. After dissolution of this oil in a mixture of ether:methanol (10:1 v/v) a saturated solution of HCl in ether was added to give, after filtration, methyl α-amino-p-methoxycarbonyl-methylphenylacetate (2.2 g, 96%) as a white solid, m.p. 189.2°-189.6° C.;

後処理

  1. customwas evaporated to dryness
  2. dissolutionThe resulting solid was dissolved in ethyl acetate
  3. extractionAfter extraction with ethyl acetate the organic layers
  4. washwere washed with brine
  5. customdried
  6. customevaporated
  7. customto give a yellow oil
  8. dissolutionAfter dissolution of this oil
  9. additionwas added
  10. customto give
  11. filtrationafter filtration, methyl α-amino-p-methoxycarbonyl-methylphenylacetate (2.2 g, 96%) as a white solid, m.p. 189.2°-189.6° C.

出典と根拠

ORDレコード
ord-9ec8b2b771ad4249893cd9784f39e532
出典データセット
uspto-grants-1998_05
特許番号
US05747499

反応ノート

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