Triethylamine → 2-(Trimethylsilyl)ethyl (S)-2-((R)-3-((R)-(3-methoxypropoxy)(phenyl)methyl)piperidine-1-carboxamido)-3-cyclohexylpropylcarbamate

HRID 1254231Notes

Reaction equation

HRID 1254231 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C@@H:7]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14](Cl)=[O:15])[CH2:9]1.[NH2:23][C@@H:24]([CH2:36][CH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1)[CH2:25][NH:26][C:27](=[O:35])[O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C@@H:7]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([NH:23][C@@H:24]([CH2:36][CH:37]2[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]2)[CH2:25][NH:26][C:27](=[O:35])[O:28][CH2:29][CH2:30][Si:31]([CH3:33])([CH3:34])[CH3:32])=[O:15])[CH2:9]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 59382894(R)-3-((R)-(3-methoxypropoxy)(phenyl)methyl)piperidine-1-carbonyl chlorideHCID 59382944(S)-2-(trimethylsilyl)ethyl 2-amino-3-cyclohexylpropylcarbamate

Product 1

HCID 866261922-(Trimethylsilyl)ethyl (S)-2-((R)-3-((R)-(3-methoxypropoxy)(phenyl)methyl)piperidine-1-carboxamido)-3-cyclohexylpropylcarbamateYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Crude (R)-3-((R)-(3-methoxypropoxy)(phenyl)methyl)piperidine-1-carbonyl chloride (60 mg, 0.184 mmol), 2-(trimethylsilyl)ethyl (S)-2-amino-3-cyclohexylpropylcarbamate (69 mg, 0.23 mmol, 1.25 equiv) and triethylamine (64 μL, 0.46 mmol, 2.5 equiv) were combined in CH2Cl2 (1 mL) at rt and left on the shaker overnight. After concentration, the product was isolated by prep HPLC to afford 2-(trimethylsilyl)ethyl (S)-2-((R)-3-((R)-(3-methoxypropoxy)-(phenyl)methyl)piperidine-1-carboxamido)-3-cyclohexyl-propylcarbamate (85.3 mg, 79%). LC-MS (3 min) tR=2.44 min, m/z 590 (M+1).

Workup

  1. concentrationAfter concentration
  2. customthe product was isolated by prep HPLC

Sources & evidence

ORD record
ord-411b436ba434431c99fb80b2d6989e5a
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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