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 1037630Notes

Reaction equation

HRID 1037630 reaction equation
[ClH:1].[CH3:2][C@@:3]([OH:35])([C:31]([CH3:34])([CH3:33])[CH3:32])[C@@H:4]1[C@:9]2([O:29][CH3:30])[C@@H:10]3[O:24][C:19]4=[C:20]([OH:23])[CH:21]=[CH:22][C:17]5=[C:18]4[C@:11]43[CH2:12][CH2:13][N:14]([CH2:25][CH:26]3[CH2:28][CH2:27]3)[C@H:15]([CH2:16]5)[C@@:6]4([CH2:7][CH2:8]2)[CH2:5]1>CC(C)=O>[CH3:2][C@@:3]([OH:35])([C:31]([CH3:34])([CH3:33])[CH3:32])[C@@H:4]1[C@:9]2([O:29][CH3:30])[C@@H:10]3[O:24][C:19]4=[C:20]([OH:23])[CH:21]=[CH:22][C:17]5=[C:18]4[C@:11]43[CH2:12][CH2:13][N:14]([CH2:25][CH:26]3[CH2:27][CH2:28]3)[C@H:15]([CH2:16]5)[C@@:6]4([CH2:7][CH2:8]2)[CH2:5]1.[ClH:1]

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;hydrochloride

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Conc. HCl (2.6 L) was added to the filtered solution of buprenorphine base (9.65 Kg) in acetone (68 L) at below 15° C. to get pH below 2.0 and stirred for 1.0-2.0 hrs. The HCl salt firmed was filtered, washed with acetone and finally leached with filtered DM water (28 L) at 80° C. and dried. Yield=8.42 Kg.

Workup

  1. customto get pH below 2.0
  2. filtrationThe HCl salt firmed was filtered
  3. washwashed with acetone
  4. customfinally leached with filtered DM water (28 L) at 80° C.
  5. customdried

Sources & evidence

ORD record
ord-24f32c6732c940fa87e77ddab1cb1687
Source dataset
uspto-grants-2013_10
Patent number
US08546572B2

Reaction notes

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