Ammonia → tert-Butyl (aminooxy)acetate

HRID 328450ノート

反応式

HRID 328450 の反応式
[C:1]([O:5][C:6]([CH2:8][O:9][N:10]1C(=O)C2=CC=CC=C2C1=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.NN.N.CCOCC>C(Cl)Cl.CO>[C:1]([O:5][C:6]([CH2:8][O:9][NH2:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 222AmmoniaHCID 3283Diethyl EtherHCID 24654Hydrazine hydrate (1:1)HCID 12919120Tert-butyl 2-(1,3-dioxoisoindolin-2-yloxy)acetate

生成物 1

HCID 12919121tert-Butyl (aminooxy)acetate

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of N-t-butoxycarbonylmethoxyphthalimide (21g) in methylene chloride (250ml) was treated with 100% hydrazine hydrate (7.6ml) in methanol (15ml), and the mixture was stirred for 1.5 hr. 5N-Ammonia solution was added to dissolve the precipitated solid. The organic layer was separated, and the aqueous layer was further extracted with methylene chloride. The combined extracts were washed with water, dried, and evaporated to give a pale-yellow solid. To this was added ether, the mixture was filtered, and the filtrate evaporated to give t-butoxycarbonylmethoxyamine as a pale yellow liquid, (8.88g, 80%); νmax. (Nujol) includes 3330, 3260 cm.-1 (NH2), 1742 cm.-1 (-COOBut); τ values (DMSO-d6) are 3.75 (-NH2), 5.96 (CH2) 8.55 (But).

後処理

  1. dissolutionto dissolve the precipitated solid
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was further extracted with methylene chloride
  4. washThe combined extracts were washed with water
  5. customdried
  6. customevaporated
  7. customto give a pale-yellow solid
  8. filtrationthe mixture was filtered
  9. customthe filtrate evaporated

出典と根拠

ORDレコード
ord-95b5638c268f48f3bfc69b454ad43d29
出典データセット
uspto-grants-1977_04
特許番号
US04017515

反応ノート

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