Hydrochloric Acid → HCID 86635169, compound

HRID 2266246Notes

Reaction equation

HRID 2266246 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)=[C:6]([C@:15]([C@@H:25]2[CH2:30][CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26]2)([OH:24])[CH2:16][CH2:17][CH2:18][NH:19][C:20]([O:22][CH3:23])=[O:21])[CH:5]=[CH:4][CH:3]=1.Cl>CC#N>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)=[C:6]([C@@:15]([OH:24])([CH:25]2[CH2:30][CH2:29][CH2:28][NH:27][CH2:26]2)[CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:21])[O:22][CH3:23])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59598490HCID 59598490, compound

Product 1

HCID 86635169HCID 86635169, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (R)-tert-butyl 3-((S)-1-(6-chloro-3′-methylbiphenyl-2-yl)-1-hydroxy-4-(methoxycarbonylamino)butyl)piperidine-1-carboxylate (600 mg, 1.13 mg) in CH3CN (18 mL) was added 2N aq HCl (15 mL) and the reaction mixture was vigorously stirred overnight at rt. The solvents were removed in vacuo to give methyl (4S)-4-(6-chloro-3′-methylbiphenyl-2-yl)-4-hydroxy-4-(piperidin-3-yl)butylcarbamate as its hydrochloride salt (500 mg, 95.8%). 1H NMR (400 MHz, CD3OD): 1.00-1.20 (m, 1H), 1.30-1.80 (m, 8H), 1.80-2.00 (m, 2H), 2.40-2.50 (d, 3H), 2.75-2.90 (t, 1H), 2.90-3.05 (m, 3H), 3.05-3.12 (t, 1H), 3.20-3.30 (m, 1H), 3.30-3.40 (m, 1H), 3.60-3.70 (d, 4H), 6.90-6.98 (d, 1H), 7.00-7.12 (m, 1H), 7.25-7.50 (m, 4H), 7.75-7.85 (d, 1H); MS (E/Z): 431 (M+H+)

Workup

  1. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-b5bf0f45e33040a9a68589d96c8c7615
Source dataset
uspto-grants-2010_12
Patent number
US07858624B2

Reaction notes

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