Hydrochloric Acid → [(4-Cyclopropylmethoxy-benzenesulfonyl)-(4-dimethylamino-benzyl)-amino]-acetic acid

HRID 1591691Notes

Reaction equation

HRID 1591691 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][N:5]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH:27]2[CH2:29][CH2:28]2)=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH3:15])[CH3:14])=[CH:9][CH:8]=1.O.[OH-].[Li+].O.Cl>C1COCC1>[CH:27]1([CH2:26][O:25][C:22]2[CH:21]=[CH:20][C:19]([S:16]([N:5]([CH2:4][C:3]([OH:30])=[O:2])[CH2:6][C:7]3[CH:8]=[CH:9][C:10]([N:13]([CH3:15])[CH3:14])=[CH:11][CH:12]=3)(=[O:18])=[O:17])=[CH:24][CH:23]=2)[CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 11224248[(4-Cyclopropylmethoxy-benzenesulfonyl)-(4-dimethylamino-benzyl)-amino]-acetic acid methyl ester

Product 1

HCID 11339094[(4-Cyclopropylmethoxy-benzenesulfonyl)-(4-dimethylamino-benzyl)-amino]-acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 74.6 g (172.4 mmol) of the compound of Stage 1.4 in 800 ml of THF, 14.5 g (345.6 mmol) of lithium hydroxide monohydrate and 400 ml of H2O are successively added at 0-5° C. After stirring for 4 h at r.t., the mixture is neutralized with aqueous 2 mol HCl at 0-5° C. and extracted with CH2Cl2 several times. The combined extracts are dried over MgSO4 and concentrated under reduced pressure to give the title compound.

Workup

  1. extractionextracted with CH2Cl2 several times
  2. dry with materialThe combined extracts are dried over MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b4ddc711db0e406ab56ee82d337b45b1
Source dataset
uspto-grants-2007_11
Patent number
US07291634B2

Reaction notes

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