Triethylamine → HCID 42633207, compound

HRID 1674687Notes

Reaction equation

HRID 1674687 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]([CH2:45]O)[CH2:9]1)=O)(C)(C)C.[CH3:47][CH2:48][N:49](CC)[CH2:50][CH3:51].OS([O-])(=O)=O.[K+]>CS(C)=O.C(Cl)Cl.O>[CH2:43]([O:42][C@H:40]([CH3:41])[CH2:39][O:38][CH2:37][C:34]1[CH:35]=[CH:36][C:31]([C@H:11]2[C@H:10]([CH2:45][N:49]3[CH2:50][CH2:51][CH2:47][CH2:48]3)[CH2:9][NH:8][CH2:13][C@@H:12]2[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)=[CH:32][CH:33]=1)[CH3:44]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 516920Potassium bisulfateHCID 42609851HCID 42609851, compound

Product 1

HCID 42633207HCID 42633207, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1 mmol of (3S,4R,5R)-4-[4-((R)-2-ethoxy-propoxymethyl)-phenyl]-3-hydroxymethyl-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-1-carboxylic acid tert-butyl ester (example 1a) in 1 ml of DMSO and 5 ml of CH2Cl2 at 0° C. are added 5 mmol of Et3N and 3 mmol of pyridine sulfur trioxide complex. The reaction mixture is allowed to stir for an additional 3 h at this temperature and then allowed to warm to RT and stirred at RT for 5 h, diluted with water and acidified by the addition of 1N KHSO4 and subsequently extracted with Et2O. The organic phases are dried over Na2SO4 and concentrated by evaporation The residue is purified by flash chromatography (SiO2 60F) to afford the title compound, which is identified based on the Rf value.

Workup

  1. stirringstirred at RT for 5 h
  2. extractionsubsequently extracted with Et2O
  3. dry with materialThe organic phases are dried over Na2SO4
  4. concentrationconcentrated by evaporation The residue
  5. customis purified by flash chromatography (SiO2 60F)

Sources & evidence

ORD record
ord-59e2f605c7414f74b4a56a66d4bdba56
Source dataset
uspto-grants-2011_08
Patent number
US08003640B2

Reaction notes

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