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Ammonia → HCID 178453744, compound

HRID 1901653
Notes
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Reaction equation

HRID 1901653 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:22][C:23]1[O:27][N:26]=[C:25]([O:28]S(C2C=CC=CC=2)(=O)=O)[CH:24]=1)[CH2:10][O:11][C:12]1[C:16]2[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=2[O:14][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.N.Cl>O1CCCC1.C(OCC)(=O)C.O>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:22][C:23]1[O:27][N:26]=[C:25]([OH:28])[CH:24]=1)[CH2:10][O:11][C:12]1[C:16]2[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=2[O:14][N:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 887MethanolHCID 233684903-[2-Tert-butoxycarbonylamino-3-(3-benzenesulfonyloxy-5-isoxazolyl)propoxy]-5-chloro-1,2-benzoisoxazole

Product 1

HCID 178453744HCID 178453744, compoundYield 102%

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.5 g of 3-[2-tert-butoxycarbonylamino-3-(3-benzenesulfonyloxy-5-isoxazolyl)propoxy]-5-chloro-1,2-benzoisoxazole in 4 ml of tetrahydrofuran is added 2.5 ml of a methanol solution (6N) of ammonia at room temperature, and they are subjected to reaction at the same temperature for 16 hours. Water and ethyl acetate are added to the reaction mixture, 1N hydrochloric acid is thereafter added to adjust the pH to 2, and after shaking, the organic layer is separated. The separated organic layer is washed with a saturated saline solution and dried over anhydrous magnesium sulfate, after which the solvent is removed by distillation under reduced pressure, to obtain 0.38 g of 3-[2-tert-butoxycarbonylamino-3-(3-hydroxy-5-isoxazolyl)propoxy]-5-chloro-1,2-benzoisoxazole having a melting point of 158.8°-160.7° C.

Workup

  1. customthey are subjected to reaction at the same temperature for 16 hours
  2. additionis thereafter added
  3. customthe organic layer is separated
  4. washThe separated organic layer is washed with a saturated saline solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customafter which the solvent is removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-3c9cfd3b50e74b4893e7ef00b3dc945c
Source dataset
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05578627

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes