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Hydrochloric Acid → (1S,2S,6R,14R,15S,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol;hydrochloride

HRID 515577
Notes
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Reaction equation

HRID 515577 reaction equation
[CH3:1][C@@:2]([OH:34])([C:30]([CH3:33])([CH3:32])[CH3:31])[C@@H:3]1[C@:8]2([O:28][CH3:29])[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]([CH2:24][CH:25]3[CH2:27][CH2:26]3)[C@H:14]([CH2:15]5)[C@@:5]4([CH2:6][CH2:7]2)[CH2:4]1.[ClH:35]>C(O)C>[CH3:1][C@@:2]([OH:34])([C:30]([CH3:33])([CH3:32])[CH3:31])[C@@H:3]1[C@:8]2([O:28][CH3:29])[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]([CH2:24][CH:25]3[CH2:26][CH2:27]3)[C@H:14]([CH2:15]5)[C@@:5]4([CH2:6][CH2:7]2)[CH2:4]1.[ClH:35]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 9848990Buprenorphine component OF alks-5461

Product 1

HCID 9848989(1S,2S,6R,14R,15S,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol;hydrochlorideYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of buprenorphine (5.1 g, 11 m mol) in ethanol (60 ml) at 50-60° C. is added concentrated hydrochloric acid to pH 2.5, the heating is maintained at 50-60° C. for 2 hours, and cooled to 10-15° C. The mixture is filtered to collect the solid. The solid is washed with cold ethanol and dried at 80° C. under 25 inch Hg of vacuum for 4 hours to give the final product (expected yield: 5.3 g; 96% Yield). This product is identical to a USP standard of Buprenorphine Hydrochloride.

Workup

  1. temperaturecooled to 10-15° C
  2. filtrationThe mixture is filtered
  3. customto collect the solid
  4. washThe solid is washed with cold ethanol
  5. customdried at 80° C. under 25 inch Hg of vacuum for 4 hours

Sources & evidence

ORD record
ord-51496f458aed40a0af0ea7f54e33c575
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09108974B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes