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

HRID 2078225
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HRID 2078225 반응식
[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]
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참가 물질

3

반응물 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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-631b60a3468340b6b1462075bb0b4f07
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07928139B2

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