Hydrochloric Acid → HCID 67435437, compound

HRID 1662976Notes

Reaction equation

HRID 1662976 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.C(N(CC)CC)C.[Cl:23][CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1.Cl>O1CCOCC1.O>[CH3:1][O:2][C:3](=[O:15])[CH2:4][N:5]([S:34]([C:31]1[CH:30]=[CH:29][C:28]([O:27][CH2:26][CH2:25][CH2:24][Cl:23])=[CH:33][CH:32]=1)(=[O:35])=[O:36])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10846084N-((4-Methoxyphenyl)methyl)glycine methyl esterHCID 218847304-(3-Chloropropoxy)benzenesulfonyl chloride

Product 1

HCID 67435437HCID 67435437, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 30.97 g (0.148 mol) of (4-methoxy-benzylamino)-acetic acid methyl ester in 200 ml of dioxane and 200 ml of H2O, 25 ml (0.178 mol) of triethylamine a solution of 43.9 g (0.163 mol) of 4-(3-chloro-propoxy)-benzenesulfonyl chloride in 100 ml of dioxane is added at 0-5° C. The mixture is allowed to warm to r.t. and stirred for 3 h. The reaction mixture is neutralized with 1N HCl and extracted with AcOEt. The combined extracts are dried over MgSO4 and concentrated under reduced pressure to give {[4-(3-chloro-propoxy)benzenesulfonyl]-(4-methoxy-benzyl)-amino}-acetic acid methyl ester; NMR (CDCl3): 2.25-2.35 (m, 2H), 3.56 (s, 3H), 3.75 (t, 2H, J=6.04 Hz), 3.79 (s, 3H), 3.9 (s, 2H), 4.2 (t, 2H, J=6.04 Hz), 4.39 (s, 2H), 6.84 (d, 2H, J=8.56 Hz), 6.99 (d, 2H, J=9.08 Hz), 7.16 (d, 2H, J=9.08 Hz), 7.83 (d, 2H, J=8.56 Hz).

Workup

  1. extractionextracted with AcOEt
  2. dry with materialThe combined extracts are dried over MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-81238693cd054cf89ac2cb5a9ce485da
Source dataset
uspto-grants-2011_10
Patent number
US08034810B2

Reaction notes

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