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Methyl chloroformate → HCID 59598490, compound

HRID 2266245
Notes
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Reaction equation

HRID 2266245 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C@:5]([C@@H:21]1[CH2:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]1)([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:8]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=1)[OH:6].CCN(CC)CC.Cl[C:42]([O:44][CH3:45])=[O:43]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:13][C:9]1[C:8]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=2)=[C:7]([C@:5]([C@@H:21]2[CH2:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]2)([OH:6])[CH2:4][CH2:3][CH2:2][NH:1][C:42]([O:44][CH3:45])=[O:43])[CH:12]=[CH:11][CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 59598487HCID 59598487, compound

Product 1

HCID 59598490HCID 59598490, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst
HCID 6344
Dichloromethane
Solvent
2×

Procedure

To a solution of (R)-tert-butyl 3-((S)-4-amino-1-(6-chloro-3′-methylbiphenyl-2-yl)-1-hydroxybutyl)piperidine-1-carboxylate (800 mg, 1.69 mmol) in anhydrous CH2Cl2 (15 mL) were added 4-dimethyaminopyridine (1.24 g, 10.17 mmol) and Et3N (2.35 mL, 16.95 mmol). The mixture was cooled with an ice bath and methyl chloroformate (0.65 mL, 8.47 mmol) in CH2Cl2 (5 mL) was added. The reaction mixture was allowed to warm slowly to rt while stirring overnight. The solvent was removed in vacuo and the residue was purified by column chromatography to afford (R)-tert-butyl 3-((S)-1-(6-chloro-3′-methylbiphenyl-2-yl)-1-hydroxy-4-(methoxycarbonylamino)butyl)piperidine-1-carboxylate (700 mg, 78%). 1H NMR (400 MHz, CD3OD): 1.00-1.70 (m, 17H), 2.30-2.50 (d, 3H), 2.50-2.70 (s, 1H), 2.90-2.31 (m, 2H), 3.50-3.52 (m, 3H), 3.80-4.20 (m, 2H), 6.0-7.15 (m, 3H), 7.15-7.40 (m, 3H), 7.50-7.70 (m, 1H); MS (E/Z): 531 (M+H+)

Workup

  1. temperatureThe mixture was cooled with an ice bath
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-b1d2e25ff13c42ceb2bce7ebaaee315a
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07858624B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes