Isobutyl chloroformate → Morphine

HRID 1283341Notes

Reaction equation

HRID 1283341 reaction equation
C(C[O:5][C:6]1[CH:7]=[CH:8][C:9]2[CH2:10][C@H:11]3[N:23]([CH3:24])[CH2:22][CH2:21][C@:17]45[C:18]=2[C:19]=1[O:20][C@H:16]4[C@@H:15]([OH:25])[CH:14]=[CH:13][C@@H:12]35)(O)=O.ClC(OCC(C)C)=O>CN(C)C=O.O>[CH:8]1[C:9]2[CH2:10][C@H:11]3[N:23]([CH2:22][CH2:21][C@@:17]45[C@H:12]3[CH:13]=[CH:14][C@H:15]([OH:25])[C@@H:16]4[O:20][C:19]([C:18]=25)=[C:6]([OH:5])[CH:7]=1)[CH3:24]

Participants

5

Reactant 2

HCID 62365Isobutyl chloroformateHCID 22791130HCID 22791130, compound

Product 1

HCID 5288826Morphine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
-15 °C

Procedure

Carboxymethyl morphine (240 mg) suspended in 8 ml dry dimethyl formamide (DMF) was cooled to -15° C and treated with 84 μl isobutyl chloroformate. The solid dissolved while stirring for 30 minutes at -15° C. Bovine serum albumin (BSA) (400 mg) dissolved in 56 ml water containing 2.6 g sodium bicarbonate was added to this solution and the mixture was kept at 0° C overnight. It was then dialyzed against distilled water with four changes of water (dialysis 1:80) and lyophilized to give 350 mg of conjugate.

Workup

  1. dissolutionThe solid dissolved
  2. additionwas added to this solution
  3. waitthe mixture was kept at 0° C overnight
  4. customIt was then dialyzed
  5. distillationagainst distilled water with four changes of water (dialysis 1:80)
  6. customto give 350 mg of conjugate

Sources & evidence

ORD record
ord-9270079be20f4dc28b4554d77e10f5db
Source dataset
uspto-grants-1976_08
Patent number
US03975237

Reaction notes

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