Sodium Hydroxide → [4-(N-benzyloxycarbonylamino)-2-nitronaphthalen-1-yl]acetic acid

HRID 431733Notes

Reaction equation

HRID 431733 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]([NH:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([CH2:24][C:25]([O:27]CC)=[O:26])=[C:16]([N+:30]([O-:32])=[O:31])[CH:15]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O.CCO>[CH2:3]([O:10][C:11]([NH:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([CH2:24][C:25]([OH:27])=[O:26])=[C:16]([N+:30]([O-:32])=[O:31])[CH:15]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59060232ethyl [4-(N-benzyloxycarbonylamino)-2-nitronaphthalen-1-yl]acetate

Product 1

HCID 18761448[4-(N-benzyloxycarbonylamino)-2-nitronaphthalen-1-yl]acetic acidYield 89%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of NaOH (0.17 g, 4.31 mmol) in H2O (20 mL) was added to a suspension of ethyl [4-(N-benzyloxycarbonylamino)-2-nitronaphthalen-1-yl]acetate (0.8 g, 1.96 mmol) in EtOH (20 mL), and the mixture was heated to reflux for 2hr. EtOH was evaporated and washed with Et2O (10 mL). The aqueous layer was acidified (pH 1) with 6 M HCl. The resulting precipitate was filtered and left out overnight to provide [4-(N-benzyloxycarbonylamino)-2-nitronaphthalen-1-yl]acetic acid (0.66 g, 89%) as an orange solid. M.p. 170-172° C. (decomp.); 1H NMR (DMSO-d6, 500 MHz) δ 8.40 (d, 8.5, 1H), 8.13 (d, 9.0, 1H), 7.67 (m, 2H), 7.55 (m, 1H), 7.41 (d, 7.5, 2H), 7.32 (t, 7.0, 2H), 7.22 (t, 8.0, 1H), 6.71 (s, 1H), 4.55 (d, 5.5, 2H), 4.04 (s, 2H); ESMS m/z 337 (M−CO2+H+), 673 ((M−CO2)×2+H+); IR (nujol) 3405, 2652, 1696, 1590, 1515, 1461, 1439, 1377, 1333, 1249, 1120, 929, 832, 792, 752, 699 cm−1. FABMS (NBA) m/z 336 (M−CO2+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2hr
  3. customEtOH was evaporated
  4. washwashed with Et2O (10 mL)
  5. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-2ae0852cfbb74ce4b3ae29977af223c1
Source dataset
uspto-grants-2003_12
Patent number
US06660742B2

Reaction notes

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