Ammonium Chloride → tert-Butyl (3(S)-{[2-(3-methoxypropoxy)benzoylamino]methyl}-4-methyl-1(S)-vinylpentyl)carbamate

HRID 507828Notes

Reaction equation

HRID 507828 reaction equation
[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[K+].[CH:11]([C@@H:13]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:14][C@H:15]([CH2:19][NH:20][C:21](=[O:34])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[O:28][CH2:29][CH2:30][CH2:31][O:32][CH3:33])[CH:16]([CH3:18])[CH3:17])=O.[Cl-].[NH4+]>C(OCC)C.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:33][O:32][CH2:31][CH2:30][CH2:29][O:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:21]([NH:20][CH2:19][C@H:15]([CH:16]([CH3:17])[CH3:18])[CH2:14][C@H:13]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:40])([CH3:41])[CH3:39])[CH:11]=[CH2:1])=[O:34]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 86613452tert-Butyl (1(S)-formyl-3(S)-{[2-(3-methoxypropoxy)benzoylamino]methyl}-4-methylpentyl)carbamate

Product 1

HCID 86613451tert-Butyl (3(S)-{[2-(3-methoxypropoxy)benzoylamino]methyl}-4-methyl-1(S)-vinylpentyl)carbamate

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

The mixture of 2.38 g of potassium bis(trimethylsilyl)amide in 50 ml of diethyl ether is cooled to 0° C., admixed with 4.04 g of methyltriphenylphosphonium bromide and stirred over 30 minutes. The solution of 1.70 g of tert-butyl (1(S)-formyl-3(S)-{[2-(3-methoxypropoxy)-benzoylamino]methyl}4-methylpentyl)carbamate in 20 ml of diethyl ether is added dropwise. The reaction mixture is stirred at room temperature over 1 hour and subsequently poured onto 1M ammonium chloride solution and extracted with tert-butyl methyl ether (2×). The combined organic phases are washed with water and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) as a slightly yellowish oil. Rf=0.36 (1:1 EtOAc-heptane); Rt=5.05 (gradient I).

Workup

  1. stirringThe reaction mixture is stirred at room temperature over 1 hour
  2. extractionextracted with tert-butyl methyl ether (2×)
  3. washThe combined organic phases are washed with water and brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-d578bfab9fb24186aa8d4264818369c0
Source dataset
uspto-grants-2010_08
Patent number
US07786307B2

Reaction notes

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