Trifluoroacetic acid → N-((6-chloro-4-hydroxy-2-oxo-1'-(phenylmethyl)-spiro[naphthalene-1,4'-piperidin]-3-yl)carbonyl)glycine

HRID 1868817Notes

Reaction equation

HRID 1868817 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:21](=[CH:22][CH:23]=1)[C:8]1([CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:10][CH2:9]1)[C:7](=[O:24])[CH:6]([C:25]([NH:27][CH2:28][C:29]([O:31]C(C)(C)C)=[O:30])=[O:26])[CH:5]2[OH:36].C(O)(C(F)(F)F)=O>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:21](=[CH:22][CH:23]=1)[C:8]1([CH2:9][CH2:10][N:11]([CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:12][CH2:13]1)[C:7](=[O:24])[C:6]([C:25]([NH:27][CH2:28][C:29]([OH:31])=[O:30])=[O:26])=[C:5]2[OH:36]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 670999521,1-dimethylethyl N-((6-chloro-4-hydroxy-2-oxo-1'-(phenylmethyl)-4H-spiro[naphthalene-1,4'-piperidin]-3-yl)carbonyl)glycinate

Product 1

HCID 57983525N-((6-chloro-4-hydroxy-2-oxo-1'-(phenylmethyl)-spiro[naphthalene-1,4'-piperidin]-3-yl)carbonyl)glycineYield 96%

Procedure

A solution of 1,1-dimethylethyl N-((6-chloro-4-hydroxy-2-oxo-1′-(phenylmethyl)-4H-spiro[naphthalene-1,4′-piperidin]-3-yl)carbonyl)glycinate (117 mg, 229 μmol) in TFA (1701 μL, 22896 μmol) was stirred at 23° C. After 25 minutes, the reaction was concentrated and the product was precipitated by addition of water (20 mL). The solid was collected by filtration, and the residue was washed with water (10 mL) and diethyl ether (5 mL), and dried under vacuum, affording 100 mg (77%) of N-((6-chloro-4-hydroxy-2-oxo-1′-(phenylmethyl)-spiro[naphthalene-1,4′-piperidin]-3-yl)carbonyl)glycine as the trifluoroacetate salt. MS m/e=455.2 (M+H)+. Calculated for C26H24ClF3N2O7 454.13.

Workup

  1. concentrationthe reaction was concentrated
  2. customthe product was precipitated by addition of water (20 mL)
  3. filtrationThe solid was collected by filtration
  4. washthe residue was washed with water (10 mL) and diethyl ether (5 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-d49f335a5b344d858fa90a319b39b1e7
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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