Benzyl chloroformate → 8alpha-Benzyloxycarbonylamino-6-methylergoline

HRID 34953Notes

Reaction equation

HRID 34953 reaction equation
[C:1](Cl)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[NH2:12][C@H:13]1[CH2:27][C@H:26]2[C@@H:16]([CH2:17][C:18]3[C:28]4[C:21](=[CH:22][CH:23]=[CH:24][C:25]2=4)[NH:20][CH:19]=3)[N:15]([CH3:29])[CH2:14]1>C(Cl)(Cl)Cl.C(O)(C)C.[OH-].[Na+]>[CH2:4]([O:3][C:1]([NH:12][C@H:13]1[CH2:27][C@H:26]2[C@@H:16]([CH2:17][C:18]3[C:28]4[C:21](=[CH:22][CH:23]=[CH:24][C:25]2=4)[NH:20][CH:19]=3)[N:15]([CH3:29])[CH2:14]1)=[O:2])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 2

HCID 10387Benzyl chloroformateHCID 67752218HCID 67752218, compound

Product 1

HCID 704178488alpha-Benzyloxycarbonylamino-6-methylergoline

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 6212ChloroformSolventHCID 14798Sodium HydroxideSolvent

Procedure

10.5 ml (75 mM) carbobenzyloxychloride are added to a suspension of 18 g (74.7 mM) 8α-amino-6-methylergoline in 1000 ml chloroform, 150 ml isopropanol and 37 ml 2N (74 mM) sodium hydroxide at room temperature. The mixture is stirred for 2 hours at room temperature. After separation of the organic phase, this is dried, filtered and concentrated. The resultant crude product is filtered through silicagel with methylene chloride/methanol (99:1) giving the heading compound as a foam.

Workup

  1. customAfter separation of the organic phase
  2. customthis is dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. filtrationThe resultant crude product is filtered through silicagel with methylene chloride/methanol (99:1)

Sources & evidence

ORD record
ord-3f87fa4d595649339559f8787de76637
Source dataset
uspto-grants-1988_08
Patent number
US04764517

Reaction notes

Loading…