Ammonium Chloride → HCID 131728262, compound

HRID 499695Notes

Reaction equation

HRID 499695 reaction equation
[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:11][O:12][C:13](=[O:43])[NH:14][CH:15]1[CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]([C:25](=[O:42])[CH2:26][C:27]([CH3:41])([CH3:40])[CH2:28][C@H:29]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH:30]=O)[CH2:16]1.[Cl-].[NH4+]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)C>[CH3:11][O:12][C:13](=[O:43])[NH:14][CH:15]1[CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]([C:25](=[O:42])[CH2:26][C:27]([CH3:41])([CH3:40])[CH2:28][C@H:29]([NH:32][C:33]([O:35][C:36]([CH3:38])([CH3:39])[CH3:37])=[O:34])[CH:30]=[CH2:1])[CH2:16]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 131728263HCID 131728263, compound

Product 1

HCID 131728262HCID 131728262, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

4.60 g of methyltriphenylphosphonium bromide are added to a solution of 2.70 g of solid potassium bis(trimethylsilyl)amide in 60 ml of diethyl ether under argon at 0° and the mixture is stirred 30 minutes at 0° C. A solution of 1.98 g of [1-(5(S)-tert-butoxycarbonylamino-3,3-dimethyl-oxo-hexanoyl)-1,2,3,4-tetrahydro-quinolin-3(R,S)-yl]-carbamic acid methyl ester in 20 ml of diethyl ether is added dropwise at 0° C. The mixture is stirred at 0° C. for 1 hour, then poured into saturated aqueous ammonium chloride solution and extracted with tert-butyl methyl ether (2×). The combined organic layers are washed with water and brine, dried over sodium sulphate, filtered and concentrated. The title compound is obtained as a white solid from the residue by means of flash chromatography (SiO2 60 F). Rf=0.28 (1:1 EtoAc-heptane); Rt=4.79 (gradient I).

Workup

  1. stirringThe mixture is stirred at 0° C. for 1 hour
  2. extractionextracted with tert-butyl methyl ether (2×)
  3. washThe combined organic layers are washed with water and brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d147c38be84f4f4b8a01b220f53d8e4d
Source dataset
uspto-grants-2010_08
Patent number
US07767690B2

Reaction notes

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