Diisopropylethylamine → HCID 57457647, compound

HRID 550998Notes

Reaction equation

HRID 550998 reaction equation
C([C:4]1[C:9]([NH:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[C:8]([N+:16]([O-:18])=[O:17])[CH:7]=[CH:6][CH:5]=1)(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:26])C=CC=CC=1.C([N:39]([CH2:43]C)C(C)C)(C)C>C(O)(C)(C)C>[N+:16]([C:8]1[C:9]2[N:10]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:43](=[O:26])[NH:39][C:4]=2[CH:5]=[CH:6][CH:7]=1)([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 57663762HCID 57663762, compound

Product 1

HCID 57457647HCID 57457647, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of methyl N-(6-carboxy-2-nitrophenyl)glycinate from Step A (6.08 g, 23.9 mmol), diphenyl phosphoryl azide (7.90 g, 28.7 mmol) and N,N-diisopropylethylamine (12.5 mL, 71.8 mmol) in tert-BuOH (40 mL) was heated at 90° C. for 90 min, then solvent was removed in vacuo. The residue was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH—100:0 to 90:10, to give the title compound in sufficient purity for use in subsequent steps. MS: m/z=252 (M+1).

Workup

  1. customsolvent was removed in vacuo
  2. customThe residue was purified by silica gel chromatography
  3. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-8d262b29c0d647bd8c967f256eaac880
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

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