Buprenorphine component OF alks-5461 → 7alpha-[(2S)-3,3-dimethyl-2-hydroxybutan-2-yl]-4,5alpha-epoxy-3,6-dihydroxy-17-methyl-6alpha,14alpha-ethanomorphinan

HRID 629839Notes

Reaction equation

HRID 629839 reaction equation
C1([CH2:4][N:5]2[CH2:25][CH2:24][C@@:12]34[C:13]5[C:18]6[CH2:19][C@@H:6]2[C@H:7]3[CH2:8][C@H:9]([C@:27]([OH:33])([C:29]([CH3:32])([CH3:31])[CH3:30])[CH3:28])[C@H:10]([OH:26])[C@@H:11]4[O:23][C:14]=5[C:15]([OH:22])=[C:16]2[CH2:21][CH2:20][C:17]2=6)CC1.C[C@@](O)(C(C)(C)C)[C@@H]1[C@]2(OC)[C@@H]3OC4=C(O)C=CC5=C4[C@]43CCN(CC3CC3)[C@H](C5)[C@@]4(CC2)C1>>[CH3:30][C:29]([CH3:32])([CH3:31])[C@:27]([C@H:9]1[CH2:8][C@H:7]2[C@@:12]34[CH2:24][CH2:25][N:5]([CH3:4])[C@@H:6]2[CH2:19][C:18]2[C:13]3=[C:14]([O:23][C@H:11]4[C@H:10]1[OH:26])[C:15]([OH:22])=[C:16]1[CH2:21][CH2:20][C:17]1=2)([OH:33])[CH3:28]

Participants

3

Reactant 2

HCID 9848990Buprenorphine component OF alks-5461HCID 8671165917-cyclopropylmethyl-7alpha-[(2S)-3,3-dimethyl-2-hydroxybutan-2-yl]-4,5alpha-epoxy-3,6-dihydroxy-6alpha,14alpha-ethanomorphinan

Product 1

HCID 867116667alpha-[(2S)-3,3-dimethyl-2-hydroxybutan-2-yl]-4,5alpha-epoxy-3,6-dihydroxy-17-methyl-6alpha,14alpha-ethanomorphinanYield 82.5%

Procedure

Compound 21 was synthesized similar to the procedure described in Example 1 for the preparation of compound 2 using compound 20 rather than compound 1. After isolation, 3.76 g of compound 21 (82.5%) was obtained with a purity of 92.7% as an off-white solid A sample was further purified by column chromatography to afford compound 21 in >99% purity as a white solid.

Workup

  1. customCompound 21 was synthesized similar to the procedure

Sources & evidence

ORD record
ord-6923c86e02c0440fb666a0c68ae0e7a3
Source dataset
uspto-grants-2016_04
Patent number
US09315514B2

Reaction notes

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