Water → HCID 18405391, compound

HRID 1833996Notes

Reaction equation

HRID 1833996 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](NCC(O)=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[O:15]([C:20]([N:22]=[N+]=[N-])=[O:21])[C:16]([CH3:19])([CH3:18])[CH3:17].[OH2:25].[O:26]1[CH2:31][CH2:30]OCC1>>[C:16]([O:15][C:20]([NH:22][CH:30]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[C:31]([OH:26])=[O:25])=[O:21])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 4

HCID 962WaterHCID 25089Glycine, N-(m-nitrophenyl)-HCID 312751,4-DioxaneHCID 61256Carbonazidic acid, 1,1-dimethylethyl ester

Product 1

HCID 18405391HCID 18405391, compound

Procedure

A mixture of m-nitrophenylglycine (58.0 g, 0.296 mol), MgO (23.92 g, 0.6 mol) and t-butoxylcarbonyl azide (85.2 g, 0.6 mol) in 50% aqueous dioxane (700 ml) was heated at 45° for 17 hours. The reaction was cooled, water (750 ml) was added, and the mixture was filtered. The filtrate was washed with ether (1000 ml), acidified to pH 3 with 40% H3PO4, and extracted with ethyl acetate. The dried extracts were evaporated to give α-t-butoxycarbonylamino-m-nitrophenylacetic acid (70.3 g).

Workup

  1. temperaturewas heated at 45° for 17 hours
  2. temperatureThe reaction was cooled
  3. filtrationthe mixture was filtered
  4. washThe filtrate was washed with ether (1000 ml)
  5. extractionextracted with ethyl acetate
  6. customThe dried extracts were evaporated

Sources & evidence

ORD record
ord-509a054a3afc4b989a6a89a432e0a846
Source dataset
uspto-grants-1978_01
Patent number
US04067976

Reaction notes

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