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Sodium Iodide → [tert-Butoxycarbonylmethyl-(2-hydroxy-phenyl)-amino]-acetic acid tert-butyl ester

HRID 2357125
Notes
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Reaction equation

HRID 2357125 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[Na+].[I-].CN(C)[C:13]1[C:22]2[C:17](=CC=C[C:21]=2N(C)C)C=CC=1.Br[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>CC#N>[C:32]([O:31][C:29](=[O:30])[CH2:28][N:1]([CH2:28][C:29]([O:31][C:22]([CH3:21])([CH3:13])[CH3:17])=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8])([CH3:35])([CH3:34])[CH3:33]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 58012-AminophenolHCID 79177tert-Butyl bromoacetateHCID 88675Proton sponge

Product 1

HCID 86596786[tert-Butoxycarbonylmethyl-(2-hydroxy-phenyl)-amino]-acetic acid tert-butyl esterYield 80%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

A solution of 2-aminophenol (10) (5.0 g, 45.8 mmol) and NaI (3.44 g, 23 mmol) in dry CH3CN (150 mL) was treated with 1,8-bis(dimethylamino) naphthalene (21.6 g, 100.8 mmol) followed by t-butyl bromoacetate (14.2 mL, 96.2 mmol) under an Ar atmosphere and stirred at reflux overnight. After the mixture was cooled to room temperature, the precipitated salts were filtered off and washed with additional EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash column chromatography, eluting with CH2Cl2/hexane/EtOAc=1:4:0.2 to yield 12.3 g (80%) of the desired product (11) as a light yellow oil. Rf=0.3 (in CH2Cl2/hexane/EtOAc=1:4:0.2); 1H NMR (300 MHz, CDCl3) δ 7.29 (dd, 7.9 and 1.5 Hz, 1H), 7.07 (m, 1H), 6.94 (dd, 8.1 and 1.5 Hz, 1H), 6.79 (m, 1H), 5.30 (s, 1H), 3.74 (s, 4H), 1.46 (s, 18H); 13C NMR (75 MHz, CDCl3) δ 171.2, 153.6, 137.4, 127.3, 126.0, 119.9, 115.6, 81.9, 57.0, 28.0; mass spectrum, calculated for C18H27NO5 (MH+) 338.2, Found 337.9.

Workup

  1. temperatureat reflux overnight
  2. filtrationthe precipitated salts were filtered off
  3. washwashed with additional EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash column chromatography
  8. washeluting with CH2Cl2/hexane/EtOAc=1:4:0.2

Sources & evidence

ORD record
ord-4f2ae7a8d1d146ae9c11422546b24775
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07759459B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes