Hydrochloric Acid → HCID 10210283, compound

HRID 412455Notes

Reaction equation

HRID 412455 reaction equation
C[O:2][C:3](=[O:42])[C@H:4]([OH:41])[CH2:5][NH:6][C:7](=[O:40])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]([C:28]2[CH:33]=[CH:32][C:31]([CH:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)=[CH:30][CH:29]=2)[C:16]([NH:18][C@H:19]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[CH3:20])=[O:17])=[CH:10][CH:9]=1.Cl>C1COCC1.CO.[OH-].[Na+]>[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([C@@H:19]([NH:18][C:16](=[O:17])[N:15]([CH2:14][C:11]2[CH:10]=[CH:9][C:8]([C:7]([NH:6][CH2:5][C@@H:4]([OH:41])[C:3]([OH:42])=[O:2])=[O:40])=[CH:13][CH:12]=2)[C:28]2[CH:29]=[CH:30][C:31]([CH:34]3[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]3)=[CH:32][CH:33]=2)[CH3:20])=[CH:26][CH:25]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 67483062HCID 67483062, compound

Product 1

HCID 10210283HCID 10210283, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

3-{4-[3-[1(S)-(4-Chlorophenyl)ethyl]-1-(4-cyclohexylphenyl)ureidomethyl]benzoylamino}-2(R)-hydroxypropionic acid methyl ester (280 mg, 0.473 mmol) was dissolved in a mixture of THF (2.5 mL) and methanol (2.5 mL) and 4 N aqueous sodium hydroxide (0.355 mL) was added. The reaction mixture was stirred at room temperature for 2 hours. The pH was adjusted to 3.0 by addition of 1 N hydrochloric acid. Solvent was removed by rotary evaporation in vacuo and the residue re-dissolved in ethyl acetate (10 mL). The organic phase was washed twice with water and once with brine, and then concentrated to dryness in vacuo leaving the title compound as a powder. Yield: 168 mg (89%).

Workup

  1. additionwas added
  2. customSolvent was removed by rotary evaporation in vacuo
  3. dissolutionthe residue re-dissolved in ethyl acetate (10 mL)
  4. washThe organic phase was washed twice with water and once with brine
  5. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-5fb9e15218d642c083ba7c3a584f758b
Source dataset
uspto-grants-2003_05
Patent number
US06562807B2

Reaction notes

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