Hydrochloric Acid → HCID 178445783, compound

HRID 2404105Notes

Reaction equation

HRID 2404105 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][NH:6][CH2:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH:19]3[CH2:24][CH2:23][CH:22]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:21][CH2:20]3)[CH:14]=2)[CH:9]=1)C.[OH-].[Li+].Cl>CO>[C:25]([C@H:22]1[CH2:21][CH2:20][C@H:19]([O:18][C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[CH:9]=[C:8]([CH2:7][NH:6][CH2:5][C:4]([OH:29])=[O:3])[CH:17]=[CH:16]3)[CH2:24][CH2:23]1)([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 70496633HCID 70496633, compound

Product 1

HCID 178445783HCID 178445783, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of {[6-(4-tert-butyl-cyclohexyloxy)-naphthalen-2-ylmethyl]-amino}-acetic acid ethyl ester (60 mg, 0.15 mmol) in methanol (1 mL) was added aqueous lithium hydroxide (4.2 M, 0.5 mL, 2 mmol) to form a white precipitate. The mixture slurry was stirred at room temperature for 3 hrs then at 50° C. for 2 hrs. The slurry was neutralized with 1 N HCl to pH 6 and the white precipitate was filtered and dried under vacuum to give white precipitate (48 mg, yield: 86%). ESI-MS: 392.3 (M+23)+; 1H NMR (400 MHz, DMSO) δ=7.77-7.82 (m, 3H), 7.48 (dd, 1H), 7.37 (d, 1H), 7.15 (dd, 1H), 4.38 (m, 1H), 4.07 (s, 2H), 3.16 (s, 2H), 2.20 (d, 2H), 1.82 (d, 2H), 1.35 (m, 2H), 1.10-1.25 (m, 3H), 0.89 (s, 9H).

Workup

  1. customto form a white precipitate
  2. waitat 50° C. for 2 hrs
  3. filtrationthe white precipitate was filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-19da5c98c9144a34867b37f08b8d2d1e
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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