Hydrochloric Acid → 6-Methoxy-2-Naphthoic Acid

HRID 1055425Notes

Reaction equation

HRID 1055425 reaction equation
O[Li].O.C(OC(N(C)[C@@H](C)C(N[C@H]1C2(CCOCC2)OC2C=CC=CC=2N(C[C:33]2[C:42]([O:43][CH3:44])=[CH:41][CH:40]=[C:39]3[C:34]=2[CH:35]=[CH:36][C:37]([C:45]([O:47]C)=[O:46])=[CH:38]3)C1=O)=O)=O)(C)(C)C.Cl>O.C1COCC1>[CH3:44][O:43][C:42]1[CH:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[CH:38]=[C:37]([C:45]([OH:47])=[O:46])[CH:36]=[CH:35]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 118574251methyl 5-(((S)-3-((S)-2-(tert-butoxycarbonyl (methyl)amino)propanamido)-4-oxo-2',3',5',6'-tetrahydro-3H-spiro[benzo[b][1,4]oxazepine-2,4'-pyran]-5 (4H)-yl)methyl)-6-methoxy-2-naphthoate

Product 1

HCID 3491816-Methoxy-2-Naphthoic AcidYield 281.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiOH.H2O (35.0 mg, 835 μmol, Eq: 5) in H2O (4 mL) was added to a solution of methyl 5-(((S)-3-((S)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-4-oxo-2′,3′,5′,6′-tetrahydro-3H-spiro[benzo[b][1,4]oxazepine-2,4′-pyran]-5 (4H)-yl)methyl)-6-methoxy-2-naphthoate (110.5 mg, 167 μmol, Eq: 1.00) in THF (3 mL). After 18 h, the mixture was poured into 1 M HCl (20 mL) and extracted with EtOAc. The combined organic extracts were washed with H2O, brine, dried over Na2SO4 and concentrated. The residue was dissolved in MeCN/H2O, and lyophilized to afford 5-((S)-3-((S)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-4-oxo-2′,3′,5′,6′-tetrahydro-3H-spiro[benzo[b][1,4]oxazepine-2,4′-pyran]-5 (4H)-yl)methyl)-6-methoxy-2-naphthoic acid (95.2 mg, 88%) of white solid which was used without purification. MS m/z 648.2 (MH+)

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic extracts were washed with H2O, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in MeCN/H2O

Sources & evidence

ORD record
ord-8b48c86f76af4c20bc24fd7a9f1fd7c8
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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