Lithium Hydroxide → HCID 67061834, compound

HRID 910806Notes

Reaction equation

HRID 910806 reaction equation
C[O:2][C:3](=[O:55])[C:4]([CH3:54])([CH3:53])[CH2:5][C@@H:6]1[CH2:11][C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][O:19][CH2:20][C@@H:21]([CH3:25])[CH2:22][O:23][CH3:24])=[CH:14][CH:13]=2)[C@@H:9]([O:26][CH2:27][C:28]2[CH:29]=[CH:30][C:31]3[O:36][CH2:35][CH2:34][N:33]([CH2:37][CH2:38][CH2:39][O:40][CH3:41])[C:32]=3[CH:42]=2)[CH2:8][N:7]1[S:43]([C:46]1[CH:51]=[CH:50][C:49]([CH3:52])=[CH:48][CH:47]=1)(=[O:45])=[O:44].[OH-].[Li+]>C1COCC1.CO>[CH3:24][O:23][CH2:22][C@H:21]([CH3:25])[CH2:20][O:19][CH2:18][C:15]1[CH:16]=[CH:17][C:12]([C@@H:10]2[C@@H:9]([O:26][CH2:27][C:28]3[CH:29]=[CH:30][C:31]4[O:36][CH2:35][CH2:34][N:33]([CH2:37][CH2:38][CH2:39][O:40][CH3:41])[C:32]=4[CH:42]=3)[CH2:8][N:7]([S:43]([C:46]3[CH:51]=[CH:50][C:49]([CH3:52])=[CH:48][CH:47]=3)(=[O:44])=[O:45])[C@H:6]([CH2:5][C:4]([CH3:54])([CH3:53])[C:3]([OH:55])=[O:2])[CH2:11]2)=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67061785HCID 67061785, compound

Product 1

HCID 67061834HCID 67061834, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 1.0 mmol of 3-[(2S,4R,5R)-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-2,2-dimethyl-propionic acid methyl ester in 10 ml of THF and 10 ml of MeOH are added 10 ml of a 3M lithium hydroxide solution. The reaction mixture is stirred for 4 h at 65° C. The organic solvents are evaporated under reduced pressure and the remaining solution is acidified with 3M aqueous HCl until pH 2. This mixture is extracted with 100 ml of EtOAc (3×). The combined organic layers are washed with brine and dried with Na2SO4. The organic layer is filtered and evaporated under reduced pressure. The residue is purified by flash chromatography (SiO2 60 F) to afford the title compound as a pale orange foam. Rf=0.28 (EtOAc/heptane/HCOOH 2:1:0.1); Rt=5.50 (gradient I).

Workup

  1. customThe organic solvents are evaporated under reduced pressure
  2. extractionThis mixture is extracted with 100 ml of EtOAc (3×)
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationThe organic layer is filtered
  6. customevaporated under reduced pressure
  7. customThe residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-d8e9458a79b8426daf838b6b24d3ec60
Source dataset
uspto-grants-2011_09
Patent number
US08022068B2

Reaction notes

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