Hydrochloric Acid → (R)-3-{4-[(4-cyclohexylphenylamino)methyl]benzoylamino}-2-hydroxypropionic acid methyl ester

HRID 967661Notes

Reaction equation

HRID 967661 reaction equation
[CH3:1][O:2][C:3](=[O:37])[C@H:4]([OH:36])[CH2:5][NH:6][C:7](=[O:35])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15](C(OC(C)(C)C)=O)[C:16]2[CH:21]=[CH:20][C:19]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:18][CH:17]=2)=[CH:10][CH:9]=1.Cl>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:37])[C@H:4]([OH:36])[CH2:5][NH:6][C:7](=[O:35])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][NH:15][C:16]2[CH:17]=[CH:18][C:19]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:20][CH:21]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69733520(R)-3-(4-{[tert-Butoxycarbonyl-(4-cyclohexylphenyl)amino]methyl}benzoylamino)-2-hydroxy-propionic acid methyl ester

Product 1

HCID 67483541(R)-3-{4-[(4-cyclohexylphenylamino)methyl]benzoylamino}-2-hydroxypropionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

(R)-3-(4-{[tert-Butoxycarbonyl-(4-cyclohexylphenyl)amino]methyl}benzoylamino)-2-hydroxy-propionic acid methyl ester was dissolved in ethyl acetate (10 mL) and dry hydrogen chloride in ethyl acetate (3 M, 10 mL) was added. The mixture was stirred at room temperature for 2 hours and concentrated in vacuo. The residue was suspended in ethyl acetate (15 mL) and concentrated. This was repeated twice. The residue was then suspended in ethyl acetate (10 mL) and placed at 5° C. overnight. The precipitate was filtered and washed with ice-cooled ethyl acetate and dried in vacuo to afford 0.62 g of (R)-3-{4-[(4-cyclohexylphenylamino)-methyl]benzoylamino}-2-hydroxypropionic acid methyl ester.

Workup

  1. concentrationconcentrated in vacuo
  2. concentrationconcentrated
  3. waitplaced at 5° C. overnight
  4. filtrationThe precipitate was filtered
  5. washwashed with ice-
  6. temperaturecooled ethyl acetate
  7. customdried in vacuo

Sources & evidence

ORD record
ord-d918e092c1444f06af2fa759ca847980
Source dataset
uspto-grants-2005_10
Patent number
US06953812B2

Reaction notes

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