Acetic Acid → HCID 21072800, compound

HRID 1372923Notes

Reaction equation

HRID 1372923 reaction equation
[CH2:1]([O:8][C:9]1[C:14]2[NH:15][C:16](=[O:19])[CH2:17][O:18][C:13]=2[C:12]([C:20](=[O:26])[CH:21](OCC)O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:27][C:28]1([CH2:31][CH2:32][N:33]2[C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=3[C:36]([CH3:44])([CH3:43])[O:35][C:34]2=[O:45])[CH2:30][CH2:29]1.[BH4-].[Na+].C(O)(=O)C>C(O)C>[CH2:1]([O:8][C:9]1[C:14]2[NH:15][C:16](=[O:19])[CH2:17][O:18][C:13]=2[C:12]([CH:20]([OH:26])[CH2:21][NH:27][C:28]2([CH2:31][CH2:32][N:33]3[C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=4[C:36]([CH3:43])([CH3:44])[O:35][C:34]3=[O:45])[CH2:30][CH2:29]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 21072805HCID 21072805, compoundHCID 21072852HCID 21072852, compound

Product 1

HCID 21072800HCID 21072800, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

900 mg (2.5 mmol) 5-benzyloxy-8-(2-ethoxy-2-hydroxy-acetyl)-4H-benzo[1,4]oxazin-3-one and 700 mg (2.7 mmol) 1-[2-(1-amino-cyclopropyl)-ethyl]-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one are dissolved in 20 mL ethanol and stirred in each case for 30 minutes at 80° C. and 50° C. The reaction mixture is cooled, combined with 200 mg (5.3 mmol) sodium borohydride and stirred for 2 hours at ambient temperature. Glacial acetic acid is added, the mixture is stirred for 10 minutes and evaporated down. The residue is taken up in dichloromethane and washed successively with potassium hydrogen sulphate solution, 15% potassium carbonate solution and sodium hydrogen carbonate solution. Then the organic phase is dried with sodium sulphate and freed from solvent. The residue is purified by column chromatography (silica gel; ethyl acetate/methanol/ammonia gradient). Recrystallisation from diisopropylether. White solid.

Workup

  1. temperatureThe reaction mixture is cooled
  2. stirringstirred for 2 hours at ambient temperature
  3. stirringthe mixture is stirred for 10 minutes
  4. customevaporated down
  5. washwashed successively with potassium hydrogen sulphate solution, 15% potassium carbonate solution and sodium hydrogen carbonate solution
  6. dry with materialThen the organic phase is dried with sodium sulphate
  7. customThe residue is purified by column chromatography (silica gel; ethyl acetate/methanol/ammonia gradient)
  8. customRecrystallisation from diisopropylether

Sources & evidence

ORD record
ord-cf71094ee7534b4da1f3c605e7e6057a
Source dataset
uspto-grants-2007_01
Patent number
US07160882B2

Reaction notes

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