Acetic Acid → (S)-methyl 2-((4-methoxybenzyl)amino)-2-phenylacetate

HRID 590789

反応式

HRID 590789 の反応式
[NH2:1][C@@H:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.CC(O)=O.[BH4-].[Na+]>CO>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH:1][C@@H:2]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([O:5][CH3:6])=[O:4])=[CH:17][CH:16]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 312444-MethoxybenzaldehydeHCID 1201451Methyl phenylglycinate, L-HCID 4311764Sodium borohydride

生成物 1

HCID 94161236(S)-methyl 2-((4-methoxybenzyl)amino)-2-phenylacetate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

To a solution of (S)-methyl 2-amino-2-phenylacetate (1.0 g, 6.06 mmol) in anhydrous MeOH (20 mL) was added 4-methoxy benzaldehyde (0.82 g, 6.06 mmol) and few drops of HOAc. After 30 min, the reaction mixture was cooled to 0° C., NaBH4 (0.69 g, 12.12 mmol) was added and the contents were stirred at ambient temperature. After 2 h, the reaction was quenched with ice cold H2O (10 mL), MeOH was removed under reduced pressure and the organic contents were extracted with EtOAc (3×25 mL). The combined organic extracts were washed with brine (1×20 mL), dried over Na2SO4, concentrated and the residue thus obtained was taken directly for step 2. MS ES+APCI calc'd. for C17H19NO3 [M+H]+ 286. Found 286.

後処理

  1. waitAfter 2 h
  2. customthe reaction was quenched with ice cold H2O (10 mL), MeOH
  3. customwas removed under reduced pressure
  4. extractionthe organic contents were extracted with EtOAc (3×25 mL)
  5. washThe combined organic extracts were washed with brine (1×20 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customthe residue thus obtained

出典と根拠

ORDレコード
ord-a8f858f06830434ea26f9db2d0852543
出典データセット
uspto-grants-2016_01
特許番号
US09233979B2

関連ノート

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