HCID 86648139, compound → HCID 42633209, compound

HRID 1674688Notes

Reaction equation

HRID 1674688 reaction equation
C(OC([N:8]1[CH2:13][C@H:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]3[O:24][CH2:23][CH2:22][N:21]([CH2:25][CH2:26][CH2:27][O:28][CH3:29])[C:20]=3[CH:30]=2)[C@@H:11]([C:31]2[CH:36]=[CH:35][C:34]([CH2:37][O:38][CH2:39][C@H:40]([O:42][CH2:43][CH3:44])[CH3:41])=[CH:33][CH:32]=2)[C@H:10]([CH:45]=O)[CH2:9]1)=O)(C)(C)C.[Cl-].[O:48]=[C:49]([N:70]1[CH2:74][CH2:73][CH2:72][CH2:71]1)[CH2:50][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O(C)[Na]>CO>[CH2:43]([O:42][C@H:40]([CH3:41])[CH2:39][O:38][CH2:37][C:34]1[CH:33]=[CH:32][C:31]([C@@H:11]2[C@@H:12]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][C:19]4[O:24][CH2:23][CH2:22][N:21]([CH2:25][CH2:26][CH2:27][O:28][CH3:29])[C:20]=4[CH:30]=3)[CH2:13][NH:8][CH2:9][C@H:10]2[CH2:45][CH2:50][C:49]([N:70]2[CH2:74][CH2:73][CH2:72][CH2:71]2)=[O:48])=[CH:36][CH:35]=1)[CH3:44]

Participants

5

Reactant 3

HCID 86648139HCID 86648139, compoundHCID 86648140HCID 86648140, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 42633209HCID 42633209, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1 mmol of (3S,4R,5R)-4-[4-((R)-2-ethoxy-propoxymethyl)-phenyl]-3-formyl-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-1-carboxylic acid tert-butyl ester (example 12b) and 1.1 mmol of (2-oxo-2-pyrrolidin-1-yl-ethyl)-triphenyl-phosphonium chloride in 5 ml MeOH is added 1.05 mmol of NaOCH3 The reaction mixture is stirred at RT overnight. The reaction mixture is quenched by addition of 0.1 N HCl and H2O. The phases are separated and the organic phase is washed with saturated aqueous NaHCO3 solution and brine. The combined aqueous phases are extracted with TBME. The combined organic layers are dried over Na2SO4 and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) and is identified based on the Rf value.

Workup

  1. customThe reaction mixture is quenched by addition of 0.1 N HCl and H2O
  2. customThe phases are separated
  3. washthe organic phase is washed with saturated aqueous NaHCO3 solution and brine
  4. extractionThe combined aqueous phases are extracted with TBME
  5. dry with materialThe combined organic layers are dried over Na2SO4
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-688acb471f284e758564526ff0cbcf5c
Source dataset
uspto-grants-2011_08
Patent number
US08003640B2

Reaction notes

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