Glutaric Acid → HCID 178449943, compound

HRID 470153Notes

Reaction equation

HRID 470153 reaction equation
[CH3:1][C:2]([N:5]([O:10])[C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:4])[CH3:3].[C:11]([OH:19])(=[O:18])[CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16].C1(C)C=CC(S([O-])(=O)=O)=CC=1.CN(C)C1C=C[NH+]=CC=1.CC(C)N=C=NC(C)C>C(O)(C)C.C(Cl)Cl>[CH3:1][C:2]([N:5]([O:10])[C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:4])[CH3:3].[C:11]([O-:19])(=[O:18])[CH2:12][CH2:13][CH2:14][C:15]([O-:17])=[O:16]

Participants

8

Reactant 5

HCID 743Glutaric AcidHCID 12734DiisopropylcarbodiimideHCID 520092Di-tert-butyl nitroxideHCID 111854944-(Dimethylamino)pyridinium 4-toluenesulfonateHCID 178435178HCID 178435178, compound

Product 1

HCID 178449943HCID 178449943, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

DTBn (0.5 mol, 209.66 g), glutaric acid (0.5 mol, 66.06 g), DPTS (0.2 mol, 58.84 g) were placed in a 3 L flask equipped with an overhead stirrer and condenser. Methylene chloride (1.2 L) was added to the flask and the contents stirred until all the solids were dispersed. DIPC (1.5 mol, 189.3 g, 234.2 mL) was added and stirring continued for 20-22 h by which time reaction mixture was viscous. The polymer was isolated by repeated precipitations from methylene chloride and isopropanol (IPA). The solid polymer was transferred to a polypropylene tray and left to dry in the hood overnight, transferred to a vacuum oven at 50° C. and dried to constant weight. The yield of poly(DTBn-glutarate) was 203 g (76%). The polymer had a molecular weight of 100 kDa and a Tg of 66° C.

Workup

  1. customequipped with an overhead stirrer and condenser
  2. additionwere dispersed
  3. stirringstirring
  4. customcontinued for 20-22 h by which time reaction mixture
  5. waitleft
  6. customto dry in the hood overnight
  7. customtransferred to a vacuum oven at 50° C.
  8. customdried to constant weight

Sources & evidence

ORD record
ord-80f0e29d0b5f403a928d0d8a9ee044b0
Source dataset
uspto-grants-2014_01
Patent number
US08629233B2

Reaction notes

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