(S)-N1-(1-cyclohexyl-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-yl)-N3-methoxy-N3-methylisophthalamide → (S)-N-(1-cyclohexyl-3-(N-methyl-N-(2-(trimethylsilyl)-ethoxycarbonyl)amino)propan-2-yl)-3-(5-methoxypentanoyl)benzamide

HRID 2355504Notes

Reaction equation

HRID 2355504 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:21][C:22](=[O:35])[C:23]2[CH:34]=[CH:33][CH:32]=[C:25]([C:26](N(OC)C)=[O:27])[CH:24]=2)[CH2:9][N:10]([CH3:20])[C:11]([O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])=[O:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:36][O:37][CH2:38][CH2:39][CH2:40][CH2:41][Mg]Cl>C1COCC1>[CH:1]1([CH2:7][C@H:8]([NH:21][C:22](=[O:35])[C:23]2[CH:34]=[CH:33][CH:32]=[C:25]([C:26](=[O:27])[CH2:41][CH2:40][CH2:39][CH2:38][O:37][CH3:36])[CH:24]=2)[CH2:9][N:10]([CH3:20])[C:11]([O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:17])[CH3:18])=[O:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 86626202(S)-N1-(1-cyclohexyl-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-yl)-N3-methoxy-N3-methylisophthalamideHCID 178495008HCID 178495008, compound

Product 1

HCID 67189747(S)-N-(1-cyclohexyl-3-(N-methyl-N-(2-(trimethylsilyl)-ethoxycarbonyl)amino)propan-2-yl)-3-(5-methoxypentanoyl)benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (S)—N1-(1-cyclohexyl-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)-amino)propan-2-yl)-N3-methoxy-N3-methylisophthalamide (0.7361 g, 1.46 mmol, 1.0 equiv) in THF (15 mL) was added 1.45 M 4-methoxybutylmagnesium chloride in THF (4 mL, 5.8 mmol, 4.0 equiv) at 0° C. under N2. After 2 h, the reaction mixture was quenched with 1 N aq HCl (15 mL) and extracted EtOAc (3×). The combined EtOAc extracts were dried over Na2SO4 and concentrated to afford crude (S)—N-(1-cyclohexyl-3-(N-methyl-N-(2-(trimethylsilyl)-ethoxycarbonyl)amino)propan-2-yl)-3-(5-methoxypentanoyl)benzamide (0.758 g), which was used in the next step without further purification. LC-MS (3 min) tR=2.34 min, m/z 555 (M+Na+), 534, 505.

Workup

  1. customthe reaction mixture was quenched with 1 N aq HCl (15 mL)
  2. extractionextracted EtOAc (3×)
  3. dry with materialThe combined EtOAc extracts were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bb910f3a69104a1891ac76b8d6d67dc6
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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