HCID 86709520, compound → HCID 86709520, compound

HRID 1848530Notes

Reaction equation

HRID 1848530 reaction equation
[CH3:1][O:2][CH:3]1[CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17][C:4]21[C:8](=[O:9])[N:7]([C:10]1[CH2:11][O:12][C:13](=[O:16])[C:14]=1[CH3:15])[CH2:6][CH2:5]2.[OH:28][CH:29]1[CH2:46][N:45]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:44][CH2:43][C:30]21[C:34](=[O:35])[N:33]([C:36]1[CH2:37][O:38][C:39](=[O:42])[C:40]=1[CH3:41])[CH2:32][CH2:31]2>C(Cl)Cl>[CH3:1][O:2][CH:3]1[CH2:20][NH:19][CH2:18][CH2:17][C:4]21[C:8](=[O:9])[N:7]([C:10]1[CH2:11][O:12][C:13](=[O:16])[C:14]=1[CH3:15])[CH2:6][CH2:5]2.[OH:28][CH:29]1[CH2:46][N:45]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:44][CH2:43][C:30]21[C:34](=[O:35])[N:33]([C:36]1[CH2:37][O:38][C:39](=[O:42])[C:40]=1[CH3:41])[CH2:32][CH2:31]2

Participants

5

Reactant 2

HCID 86709520HCID 86709520, compoundHCID 86709522HCID 86709522, compound

Product 2

HCID 86709520HCID 86709520, compoundHCID 86709523HCID 86709523, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 6-methoxy-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate (CIS, faster) (2.17 g, 5.70 mmol) in methylene chloride (7 mL) was added trifluoroacetic (7 mL, 91 mmol) and the resulting solution was stirred at rt for 2 h. After concentration the residue was basified on ion exchange column washing with methanol first, then eluted with 1 N ammonia in methanol to give 6-methoxy-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one (CIS, faster). LC/MS: (M+1)+: 281.11.

Workup

  1. concentrationAfter concentration the residue
  2. washwashing with methanol first
  3. washeluted with 1 N ammonia in methanol

Sources & evidence

ORD record
ord-e222e85e55c641c18a94b70b8de61f9d
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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