Acetone → HCID 22063465, compound

HRID 1666177Notes

Reaction equation

HRID 1666177 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:20](=[O:26])[CH:21](OCC)O)[C:12]2[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=2[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:27]([O:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][C:37]([NH2:40])([CH3:39])[CH3:38])=[CH:32][CH:31]=1)[CH3:28].[BH4-].[Na+].CC(C)=O>C(O)C.C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:20]([OH:26])[CH2:21][NH:40][C:37]([CH3:38])([CH3:39])[CH2:36][C:33]2[CH:34]=[CH:35][C:30]([O:29][CH2:27][CH3:28])=[CH:31][CH:32]=2)[C:12]2[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=2[CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 22063474HCID 22063474, compoundHCID 22063492HCID 22063492, compound

Product 1

HCID 22063465HCID 22063465, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

2.14 g (6.0 mmol) of 6-benzyloxy-8-(2-ethoxy-2-hydroxyacetyl)-4H-benzo[1,4]oxazin-3-one and 1.0 g (5.2 mmol) of 2-(4-ethoxyphenyl)-1,1-dimethylethylamine are stirred in 40 mL ethanol for one hour at 50° C.-80° C. After cooling to ambient temperature, 0.23 g (6.0 mmol) of sodium borohydride are added and the mixture is stirred for a further hour. The reaction mixture is combined with 5 mL acetone, stirred for 30 minutes, acidified with glacial acetic acid, and evaporated down. The residue is combined with water and ethyl acetate and made alkaline. The organic phase is separated off, washed with water, dried with sodium sulfate, and freed from solvent in vacuo. The residue is dissolved again in ethyl acetate and water, combined with concentrated hydrochloric acid, and diluted with diethyl ether. The solid precipitated is suction filtered and washed with diethyl ether. White solid. Yield: 2.0 g (61%, hydrochloride); melting point: 214° C.-216° C.

Workup

  1. stirringstirred for 30 minutes
  2. customevaporated down
  3. customThe organic phase is separated off
  4. washwashed with water
  5. dry with materialdried with sodium sulfate
  6. dissolutionThe residue is dissolved again in ethyl acetate
  7. additiondiluted with diethyl ether
  8. customThe solid precipitated
  9. filtrationfiltered
  10. washwashed with diethyl ether

Sources & evidence

ORD record
ord-1d7d0297959d4f3780c350cd04f2cfa0
Source dataset
uspto-grants-2011_10
Patent number
US08044046B2

Reaction notes

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