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Dimethylformamide → Buprenorphine component OF alks-5461

HRID 881992
Notes
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Reaction equation

HRID 881992 reaction equation
[CH3:1][C@@:2]([OH:30])([C:26]([CH3:29])([CH3:28])[CH3:27])[C@@H:3]1[C@@:8]2([O:24][CH3:25])[C@@H:9]3[O:23][C:18]4=[C:19]([OH:22])[CH:20]=[CH:21][C:16]5=[C:17]4[C@:10]43[CH2:11][CH2:12][NH:13][C@H:14]([CH2:15]5)[C@@:5]4([CH2:6][CH2:7]2)[CH2:4]1.C(=O)(O)[O-].[Na+].[CH:36]1([CH2:39]Br)[CH2:38][CH2:37]1.CN(C=O)C>CO.O>[CH3:1][C@@:2]([OH:30])([C:26]([CH3:29])([CH3:28])[CH3:27])[C@@H:3]1[C@:8]2([O:24][CH3:25])[C@@H:9]3[O:23][C:18]4=[C:19]([OH:22])[CH:20]=[CH:21][C:16]5=[C:17]4[C@:10]43[CH2:11][CH2:12][N:13]([CH2:39][CH:36]3[CH2:38][CH2:37]3)[C@H:14]([CH2:15]5)[C@@:5]4([CH2:6][CH2:7]2)[CH2:4]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228Dimethylformamide2×HCID 81503BromomethylcyclopropaneHCID 114976NorbuprenorphineHCID 516892Sodium Bicarbonate

Product 1

HCID 9848990Buprenorphine component OF alks-5461Yield 56.1%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

A mixture of 11.5 g of norbuprenorphine, 4.6 g of sodium bicarbonate, 4.85 g of cyclopropylmethyl bromide (1% butenyl bromide in it by GC) and 46 ml of dry DMF is heated in an oilbath at 80-100° C. for 4 hours until the reaction is substantially complete. The reaction mixture is transferred to a dropping funnel, with minimal DMF as a wash. The reaction mixture is added over 5 minutes to 160 ml of water, with mechanical stirring. (Adding water to the reaction yields a gum). The mixture is stirred for about 10 minutes and filtered. The filter cake is washed with 20 ml water. The HPLC will show about 90% by area of desired product, and 0.2-0.5% of an N-butenyl substituted impurity. The resulting product is dried, yielding about 12 g. The resulting product is boiled in 30 ml of methanol for about 30 minutes, cooled, and filtered to yield about 7.3 g buprenorphine.

Workup

  1. customyields a gum)
  2. filtrationfiltered
  3. washThe filter cake is washed with 20 ml water
  4. customThe resulting product is dried
  5. customyielding about 12 g
  6. temperaturecooled
  7. filtrationfiltered

Sources & evidence

ORD record
ord-665878874a614695aa8a58ab4b5d41f8
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08993764B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes