Ammonium Chloride → 2-(trimethylsilyl)ethyl (S)-2-(3-(1-hydroxy-5-methoxy-1-phenylpentyl)cyclohexanecarboxamido)-3-cyclohexylpropyl-methylcarbamate

HRID 2355360Notes

Reaction equation

HRID 2355360 reaction equation
[C:1]([CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15]([NH:17][C@@H:18]([CH2:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[CH2:19][N:20]([CH3:30])[C:21](=[O:29])[O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])=[O:16])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:38][O:39][CH2:40][CH2:41][CH2:42][CH2:43][Mg]Cl.C([O-])(O)=O.[Na+].[NH4+].[Cl-]>C1COCC1>[OH:8][C:1]([CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15]([NH:17][C@@H:18]([CH2:31][CH:32]2[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]2)[CH2:19][N:20]([CH3:30])[C:21](=[O:29])[O:22][CH2:23][CH2:24][Si:25]([CH3:27])([CH3:28])[CH3:26])=[O:16])[CH2:10]1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:43][CH2:42][CH2:41][CH2:40][O:39][CH3:38]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 671917252-(trimethylsilyl)ethyl (S)-2-(3-benzoylcyclohexanecarboxamido)-3-cyclohexylpropylmethylcarbamateHCID 178495008HCID 178495008, compound

Product 1

HCID 866261942-(trimethylsilyl)ethyl (S)-2-(3-(1-hydroxy-5-methoxy-1-phenylpentyl)cyclohexanecarboxamido)-3-cyclohexylpropyl-methylcarbamateYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of 2-(trimethylsilyl)ethyl (S)-2-(3-benzoylcyclohexanecarboxamido)-3-cyclohexylpropylmethylcarbamate (111 mg, 0.21 mmol) in dry THF (2 mL) was cooled to −70° C. and methoxybutylmagnesium chloride in THF (0.5 mL of 2 M, 1.0 mmol) was added dropwise over 2 min. The cooling bath was allowed to expire and the mixture was stirred as it warmed to rt. After 2 h, the mixture was poured into sat'd aqueous NaHCO3 (20 mL) and sat'd aqueous NH4Cl (20 mL) was added. The mixture was extracted with EtOAc (2×50 mL). The combined organic extracts were washed with brine (15 mL), dried over Na2SO4 and evaporated under reduced pressure to leave crude 2-(trimethylsilyl)ethyl (S)-2-(3-(1-hydroxy-5-methoxy-1-phenylpentyl)cyclohexanecarboxamido)-3-cyclohexylpropyl-methylcarbamate as an oil (124 mg, 95%). MS ESI+ve m/z 617 (M+1).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with EtOAc (2×50 mL)
  3. washThe combined organic extracts were washed with brine (15 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0caa13836f3a4224b86648a3f13cd1cb
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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