Water → HCID 54026547, compound

HRID 1459428Notes

Reaction equation

HRID 1459428 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([N:16]2[CH2:21][CH2:20][C:19]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])([CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[CH2:18][CH2:17]2)=[O:15])=[C:9]([CH3:35])[CH:8]=1)C.[Li+].[OH-].O.C1COCC1>CO>[CH3:33][C:31]([CH3:34])([O:30][C:28]([C:19]1([CH:22]2[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]2)[CH2:20][CH2:21][N:16]([C:14]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:36])=[O:3])=[CH:8][C:9]=2[CH3:35])=[O:15])[CH2:17][CH2:18]1)=[O:29])[CH3:32]

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86753477HCID 86753477, compound

Product 1

HCID 54026547HCID 54026547, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 25 mL round bottomed flask a solution of ethyl-4-[(4-(1,1-dimethylethoxycarbonyl)-4,4'-bipiperidinyl-1-carbonyl)amino]-3-methylphenoxyacetate (31-4) (100 mg, 0.2 mmol), 1M LiOH, (0.6 mL, 0.6 mmol), H2O (5 mL), THF (5 mL), and MeOH (5 mL) was stirred at ambient temperature 3 h. The reaction was concentrated in vacuo, then dissolved in CHCl3 (20 mL). The CHCl3 extract was washed (1N HCl, H2O, and brine), dried (NaSO4), filtered, and concentrated to yield 4-[(4-(1,1-dimethylethoxycarbonyl)-4,4'-bipiperidinyl-1-carbonyl)amino]-3-methylphenoxyacetic acid (31-5). 1H NMR (CDCl3): δ 1.22 (br m, 6H), 1.46 (s, 9H), 1.6 (br m, 4H), 2.2 (s, 3H), 2.6 (br t, 2H), 2.79 (t, j=11 Hz, 2H), 4.0 (br m, 5H), 4.58 (s, 2H), 6.1 (dd, j=9, 2 Hz, 1H), 6.75 (d, j=2 Hz, 1H), 7.21 (d, j=9 Hz, 1H), 8.1 (s, 1H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutiondissolved in CHCl3 (20 mL)
  3. extractionThe CHCl3 extract
  4. washwas washed (1N HCl, H2O, and brine)
  5. dry with materialdried (NaSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-efceceb38a7c49beb272c98c04d3448f
Source dataset
uspto-grants-1998_12
Patent number
US05854245

Reaction notes

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