Oxytocin acetate → Oxytocin

HRID 539418Notes

Reaction equation

HRID 539418 reaction equation
[CH3:1][CH2:2][C@@H:3]([C@@H:5]1[NH:29][C:27](=[O:28])[C@H:26]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)[NH:25][C:23](=[O:24])[C@@H:22]([NH2:38])[CH2:21][S:20][S:19][CH2:18][C@@H:17]([C:39]([N:41]2[C@H:45]([C:46]([NH:48][C@H:49]([C:54]([NH:56][CH2:57][C:58]([NH2:60])=[O:59])=[O:55])[CH2:50][CH:51]([CH3:53])[CH3:52])=[O:47])[CH2:44][CH2:43][CH2:42]2)=[O:40])[NH:16][C:14](=[O:15])[C@H:13]([CH2:61][C:62]([NH2:64])=[O:63])[NH:12][C:10](=[O:11])[C@H:9]([CH2:65][CH2:66][C:67]([NH2:69])=[O:68])[NH:8][C:6]1=[O:7])[CH3:4].CC(O)=O>CCOC(C)=O.CO>[CH3:1][CH2:2][C@@H:3]([C@@H:5]1[NH:29][C:27](=[O:28])[C@H:26]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)[NH:25][C:23](=[O:24])[C@@H:22]([NH2:38])[CH2:21][S:20][S:19][CH2:18][C@@H:17]([C:39]([N:41]2[C@H:45]([C:46]([NH:48][C@H:49]([C:54]([NH:56][CH2:57][C:58]([NH2:60])=[O:59])=[O:55])[CH2:50][CH:51]([CH3:53])[CH3:52])=[O:47])[CH2:44][CH2:43][CH2:42]2)=[O:40])[NH:16][C:14](=[O:15])[C@H:13]([CH2:61][C:62]([NH2:64])=[O:63])[NH:12][C:10](=[O:11])[C@H:9]([CH2:65][CH2:66][C:67]([NH2:69])=[O:68])[NH:8][C:6]1=[O:7])[CH3:4]

Participants

4

Reactant 1

HCID 12004215Oxytocin acetate

Product 1

HCID 439302OxytocinYield 71.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

PLGA polymer (MW 13,000, 180 mg) was dissolved in EtOAc (900 μL). Oxytocin acetate (20 mg) was dissolved in MeOH (100 μL) and added to the polymer solution yielding a milky suspension as the organic phase. The resulting organic phase was combined with a 1% PVA aqueous phase containing 5% EtOAc to provide an emulsion. The emulsion was collected directly into a 10 mM sodium phosphate (pH 8, 0° C., 150 mL) solvent extraction solution and stirred for four hours while warming to room temperature to extract EtOAc. Hardened microparticles were collected by filtration, washed with water, air dried and stored at 4° C. This provided formulation BL (143 mg, 71.5% yield) with a median particle size 44.0 μm. The core load (1.67%), encapsulation efficiency (16.7%) and in vitro burst (46.3%) were determined by RP-HPLC assay.

Workup

  1. additionadded to the polymer solution
  2. customyielding a milky suspension as the organic phase
  3. customto provide an emulsion
  4. customThe emulsion was collected directly into a 10 mM sodium phosphate (pH 8, 0° C., 150 mL) solvent extraction solution
  5. extractionto extract EtOAc
  6. filtrationHardened microparticles were collected by filtration
  7. washwashed with water, air
  8. customdried
  9. customstored at 4° C

Sources & evidence

ORD record
ord-d3c5e827515f40ee88174b21c6719394
Source dataset
uspto-grants-2014_10
Patent number
US08871269B2

Reaction notes

Loading…