Triethylamine → 2-(4-((((Tert-butoxy)carbonyl)amino)methyl)phenyl)acetic acid

HRID 237163Notes

Reaction equation

HRID 237163 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1.[C:14]([O:18][C:19](ON=C(C1C=CC=CC=1)C#N)=[O:20])([CH3:17])([CH3:16])[CH3:15].C(N(CC)CC)C>O1CCOCC1>[C:14]([O:18][C:19]([NH:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1)=[O:20])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 53407881(4-(Aminomethyl)phenyl)acetic acid--hydrogen chloride (1/1)

Product 1

HCID 27559832-(4-((((Tert-butoxy)carbonyl)amino)methyl)phenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 7.76 g (38.5 mmol) of 4-aminomethylphenylacetic acid hydrochloride, 10.42 g (42.3 mmol) of 2-t-butoxycarbonyloxyimino-2-phenylacetonitrile and 13.33 ml (96.2 mmol) of triethylamine in 60 ml of 50% aqueous dioxane was stirred for 2.5 hours at ambient temperature. The solvent was removed, 25 ml of water and 50 ml of ethyl acetate were added and the layers were separated. The aqueous phase was extracted with ethyl acetate then stirred with ethyl acetate and acidified to pH 1-1.5 with 3 N hydrochloric acid. The mixture was then extracted three times with ethyl acetate and the combined extracts were washed with water, dried (MgSO4) and evaporated to give 4-(N-t-butoxycarbonylaminomethyl)phenylacetic acid, m.p. 108°-110°.

Workup

  1. customThe solvent was removed
  2. addition25 ml of water and 50 ml of ethyl acetate were added
  3. customthe layers were separated
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. stirringthen stirred with ethyl acetate
  6. extractionThe mixture was then extracted three times with ethyl acetate
  7. washthe combined extracts were washed with water
  8. dry with materialdried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-5f6ab50a9f944ab1a26418257dc61b2f
Source dataset
uspto-grants-1979_06
Patent number
US04159373

Reaction notes

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