Trifluoroacetic acid → HCID 68755676, compound

HRID 336213Notes

Reaction equation

HRID 336213 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].C(OC([N:15]1[C@@H:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@@H:19]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:18][C:17](=[O:33])[C@@H:16]1[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][Cl:39])=O)(C)(C)C.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[F:4][C:3]([F:6])([F:5])[C:1]([OH:7])=[O:2].[Cl:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][C@H:16]1[C:17](=[O:33])[O:18][C@H:19]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C@H:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:15]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 10961504(3S,5S,6R)-3-(5-Chloro-pentyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid tert-butyl ester

Product 1

HCID 68755676HCID 68755676, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of TFA in DCM (20%, 60 mL) is added at 0° C. to (3S,5S,6R)-3-(5-chloro-pentyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid tert-butyl ester (8.0 g, 17.5 mmol). The reaction mixture is slowly warmed up to room temperature and stirred for 4 hours. The reaction mixture is poured into a saturated K2CO3 solution, the two phases are separated and the water phase is extracted with DCM twice. The combined organic phases are dried over anhydrous Na2SO4 and removal of the solvent under reduced pressure affords 6.0 g of (3S,5S,6R)-3-(5-Chloro-pentyl)-5,6-diphenyl-morpholin-2-one trifluoroacetate.

Workup

  1. customthe two phases are separated
  2. extractionthe water phase is extracted with DCM twice
  3. dry with materialThe combined organic phases are dried over anhydrous Na2SO4 and removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-1f4cdfa1bf654399ac3918463bcb7f1c
Source dataset
uspto-grants-2014_11
Patent number
US08889670B2

Reaction notes

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