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

HRID 412459Notes

Reaction equation

HRID 412459 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-hydroxypropionic 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-10ea9d4c6781483eaeba3466dd7d3087
Source dataset
uspto-grants-2003_05
Patent number
US06562807B2

Reaction notes

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