Lithium Hydroxide → {[4-(3-Chloro-propoxy)-benzenesulfonyl]-(4-methoxybenzyl)-amino}-acetic acid

HRID 722449Notes

Reaction equation

HRID 722449 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][N:5]([S:15]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][Cl:28])=[CH:20][CH:19]=1)(=[O:17])=[O:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.[Li+].[OH-]>CO.C1COCC1.O>[Cl:28][CH2:27][CH2:26][CH2:25][O:24][C:21]1[CH:20]=[CH:19][C:18]([S:15]([N:5]([CH2:4][C:3]([OH:29])=[O:2])[CH2:6][C:7]2[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=2)(=[O:17])=[O:16])=[CH:23][CH:22]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 67435437HCID 67435437, compound

Product 1

HCID 21884785{[4-(3-Chloro-propoxy)-benzenesulfonyl]-(4-methoxybenzyl)-amino}-acetic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 59.7 g (0.135 mol) of {[4-(3-chloro-propoxy)-benzenesulfonyl]-(4-methoxybenzyl)-amino}-acetic acid methyl ester in 500 ml of MeOH, 500 ml of THF and 200 ml of H2O, 11.3 g of LiOH:H2O (0.27 mol) is added at 0–5° C. The mixture is allowed to warm to r.t. and stirred for 4 h. The reaction mixture is concentrated under reduced pressure and diluted with H2O and AcOEt. After acidifying with 2N HCl at 0–5° C., the mixture is extracted with AcOEt. The combined extracts are washed with brine and concentrated under reduced pressure to give {[4-(3-chloro-propoxy)-benzenesulfonyl]-(4-methoxy-benzyl)-amino]-acetic acid; NMR (CDCl3): 2.25–2.29 (m, 2H), 3.75 (t, 2H, J=6 Hz), 3.79 (s, 3H), 3.91 (s, 2H), 4.19 (t, 2H, J=6 Hz), 4.38 (s, 2H), 6.84 (d, 2H, J=8.56 Hz), 6.99 (d, 2H, J=8.56 Hz), 7.13 (d, 2H, J=9.04 Hz), 7.82 (d, 2H, J=9.04 Hz).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. additiondiluted with H2O and AcOEt
  3. customAfter acidifying with 2N HCl at 0–5° C.
  4. extractionthe mixture is extracted with AcOEt
  5. washThe combined extracts are washed with brine
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d12c0405ef1b42aba2d785a6680e479b
Source dataset
uspto-grants-2006_11
Patent number
US07138432B1

Reaction notes

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