Sodium Bicarbonate → HCID 15871735, compound

HRID 1738904Notes

Reaction equation

HRID 1738904 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][C:13]([CH3:34])([CH3:33])[CH2:14][O:15][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[C:10](=[O:35])[C@@H:9]([CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[O:8][C@H:7]([C:42]3[C:51]4[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=4)[CH:45]=[CH:44][CH:43]=3)[C:6]=2[CH:52]=1.C(=O)(O)[O-].[Na+]>C(#N)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][C:13]([CH3:33])([CH3:34])[CH2:14][OH:15])[C:10](=[O:35])[C@@H:9]([CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[O:8][C@H:7]([C:42]3[C:51]4[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=4)[CH:45]=[CH:44][CH:43]=3)[C:6]=2[CH:52]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 131721401HCID 131721401, compound

Product 1

HCID 15871735HCID 15871735, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Ethyl trans-7-chloro-5-(1-naphthyl)-1-(3-tert-butyldiphenylsilyloxy-2,2-dimethylpropyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetate (8.52 g, 11.62 mmol) was dissolved in acetonitrile (200 ml). A solution of HF in water (50%, 50 ml) was added at room temperature. Stirring for 18 hours was followed by hydrolysis with saturated sodium bicarbonate and repeated extraction of the aqueous layer with dichloromethane. The combined organic layers were dried with MgSO4. The filtrate was concentrated under reduced pressure, and the residue was purified by flash chromatography (dichloromethane/methanol 99:1) to give the title compound (4.64 g, 81%) as a colorless solid.

Workup

  1. extractionextraction of the aqueous layer with dichloromethane
  2. dry with materialThe combined organic layers were dried with MgSO4
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by flash chromatography (dichloromethane/methanol 99:1)

Sources & evidence

ORD record
ord-08d848fe35964a42bea39c5a9339fcc6
Source dataset
uspto-grants-1999_10
Patent number
US05965553

Reaction notes

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