Sodium Hydroxide → 8-({[(Tert-butoxy)carbonyl]amino}methyl)-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

HRID 376804Notes

Reaction equation

HRID 376804 reaction equation
[C:1]([NH:8][CH2:9][CH:10]1[C:19]2[CH:18]=[C:17]([C:20]([O:22]C)=[O:21])[CH:16]=[CH:15][C:14]=2[CH2:13][CH2:12][CH2:11]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-].[Na+].C(NCC1(C(O)=O)C=CC2CCCCC=2C1)(OC(C)(C)C)=O>C(O)C.O>[C:1]([NH:8][CH2:9][CH:10]1[C:19]2[CH:18]=[C:17]([C:20]([OH:22])=[O:21])[CH:16]=[CH:15][C:14]=2[CH2:13][CH2:12][CH2:11]1)([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 19359193methyl N-(BOC)-8-aminomethyl-5,6,7,8-tetrahydro-2-naphthoateHCID 70063253N-(BOC)-2-aminomethyl-5,6,7,8-tetrahydro-2-naphthoic acid

Product 1

HCID 193591728-({[(Tert-butoxy)carbonyl]amino}methyl)-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Part E--To a solution of methyl N-(BOC)-8-aminomethyl-5,6,7,8-tetrahydro-2-naphthoate (0.50 g, 0.0016 mol) in ethanol (12.5 mL) was added, dropwise, a solution of sodium hydroxide (0.50 g) in water (12.5 mL). All was stirred a reflux over 4 hours. The reaction mixture was concentrated to half volume and then acidified to a pH equal to 1.0 using hydrochloric acid (1N). The residue was purified by flash chromatography using a gradient of hexane:ethyl acetate::1:1 to ethyl acetate to ethyl acetate: methanol::9:1 to give the racemic mixture of the title compound, N-(BOC)-2-aminomethyl-5,6,7,8-tetrahydro-2-naphthoic acid (0.19 g, 0.00062 mol, 39%) as a white solid. mp=172-176° C.; 1H NMR (DMSO) d 7.8 (s, 1H), 7.65 (d, 1H, J=8.1 Hz), 7.15 (d, 1H, J=8.1 Hz), 7.1-7.0 (m, 1H), 3.2-3.1 (m, 2H), 3.0-2.7 (m, 4H), 1.8-1.6 (m, 4H), 1.4 (s, 9H).

Workup

  1. temperaturea reflux over 4 hours
  2. concentrationThe reaction mixture was concentrated to half volume
  3. customThe residue was purified by flash chromatography
  4. customethyl acetate::1:1 to ethyl acetate to ethyl acetate: methanol::9:1 to give

Sources & evidence

ORD record
ord-7b4e5a8dceec4ced9d60d5b489837aab
Source dataset
uspto-grants-2000_02
Patent number
US06022523

Reaction notes

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