1,1-Dimethylethyl N-((4-hydroxy-7-methoxy-2-oxo-2',3',5',6'-tetrahydro-spiro[naphthalene-1,4'-pyran]-3-yl)carbonyl)glycinate → N-((4-Hydroxy-7-(methyloxy)-2-oxo-2',3',5',6'-tetrahydro-spiro[naphthalene-1,4'-pyran]-3-yl)carbonyl)glycine

HRID 2078082Notes

Reaction equation

HRID 2078082 reaction equation
[OH:1][C:2]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:5]2([CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)[C:4](=[O:19])[C:3]=1[C:20]([NH:22][CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])=[O:21]>C(O)(C(F)(F)F)=O>[OH:1][C:2]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:5]2([CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)[C:4](=[O:19])[C:3]=1[C:20]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:21]

Participants

3

Reactant 1

HCID 670998131,1-Dimethylethyl N-((4-hydroxy-7-methoxy-2-oxo-2',3',5',6'-tetrahydro-spiro[naphthalene-1,4'-pyran]-3-yl)carbonyl)glycinate

Product 1

HCID 57983439N-((4-Hydroxy-7-(methyloxy)-2-oxo-2',3',5',6'-tetrahydro-spiro[naphthalene-1,4'-pyran]-3-yl)carbonyl)glycineYield 92.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 1,1-dimethylethyl N-((4-hydroxy-7-methoxy-2-oxo-2′,3′,5′,6′-tetrahydro-spiro[naphthalene-1,4′-pyran]-3-yl)carbonyl)glycinate (0.36 g, 0.9 mmol) in 2 mL TFA was stirred at room temperature for 30 minutes, M+1=362, M−1=360. The mixture was concentrated and then triturated in DCM/hexane (5:10). The solid was filtered, washed with 10 mL DCM/hexane (5:10), and dried under high vacuum to give 0.3 g of the product as an off-white solid. MS (m/z)=362 (M+H)+. Calculated for C18H19NO7 361.12.

Workup

  1. concentrationThe mixture was concentrated
  2. customtriturated in DCM/hexane (5:10)
  3. filtrationThe solid was filtered
  4. washwashed with 10 mL DCM/hexane (5:10)
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-9332456c85e342f0b0260cd189dd2bfe
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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