4-Methylmorpholine → 2-[N-(alpha-(Isopropylthio)-N-(benzyloxycarbonyl)-glycinyl)amino]benzophenone

HRID 1080377Notes

Reaction equation

HRID 1080377 reaction equation
[CH:1]([S:4][CH:5]([C:17]([OH:19])=O)[NH:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])([CH3:3])[CH3:2].CN1CCOCC1.C(OC(Cl)=O)C(C)C.[NH2:35][C:36]1[CH:49]=[CH:48][CH:47]=[CH:46][C:37]=1[C:38]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:39]>C(Cl)Cl>[CH:1]([S:4][CH:5]([C:17]([NH:35][C:36]1[CH:49]=[CH:48][CH:47]=[CH:46][C:37]=1[C:38]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:39])=[O:19])[NH:6][C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 760802-AminobenzophenoneHCID 11346620Acetic acid, [(1-methylethyl)thio][[(phenylmethoxy)carbonyl]amino]-

Product 1

HCID 138095072-[N-(alpha-(Isopropylthio)-N-(benzyloxycarbonyl)-glycinyl)amino]benzophenone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

α-(isopropylthio)-N-(benyloxycarbonyl)glycine 22B was dissolved in methylene chloride (200 mL) under nitrogen atmosphere at 0° C. in a three necked flask carrying an additional funnel. To the stirred solution was added N-methylmorpholine (2.11 mL, 19.3 mmol) followed by isobutylchloroformate (2.48 mL, 19.2 mmol). This was stirred for 15 minutes at 0° C. and then heated to reflux. To the refluxing reaction mixture was added a solution of 2-aminobenzophenone 23 (3.59 g, 18.19 mmol) in dry methylene chloride (26 mL) over 20 minutes. The reaction mixture was stirred for 20 more minutes after the addition and then left stirring overnight at room temperature. The reaction mixture was washed with 10% citric acid, saturated sodium bicarbonate solution and brine, then dried over magnesium sulphate. Solvent evaporated at reduced pressure to give 9.30 g of the crude product 24. This was used without further purification.

Workup

  1. temperatureheated to reflux
  2. customTo the refluxing reaction mixture
  3. stirringThe reaction mixture was stirred for 20 more minutes
  4. additionafter the addition
  5. waitleft
  6. stirringstirring overnight at room temperature
  7. washThe reaction mixture was washed with 10% citric acid, saturated sodium bicarbonate solution and brine
  8. dry with materialdried over magnesium sulphate
  9. customSolvent evaporated at reduced pressure

Sources & evidence

ORD record
ord-53a3846f38d14093aec7ce51113d2a2f
Source dataset
uspto-grants-1996_12
Patent number
US05580979

Reaction notes

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