Hydrochloric Acid → HCID 11776526, compound

HRID 1957776Notes

Reaction equation

HRID 1957776 reaction equation
C([NH:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[C:15](=[O:33])[CH2:16][C@H:17]1[C:21](=[O:22])[O:20]C[N:18]1C(OCC1C=CC=CC=1)=O)(=O)C(C)(C)C.Cl.O>CC(O)=O>[NH2:18][C@@H:17]([CH2:16][C:15]([C:9]1[CH:10]=[C:11]([Cl:14])[CH:12]=[CH:13][C:8]=1[NH2:7])=[O:33])[C:21]([OH:22])=[O:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 10552425HCID 10552425, compound

Product 1

HCID 11776526HCID 11776526, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A stirred mixture of (S)-(+)-N-pivaloyl-2-[1-oxo-2-[3-(benzyloxycarbonyl)-5-oxo-oxazolidin-4-yl]ethyl]-4-chloro aniline (1.06 g, 2.24 mmol), 37% HCl (20 ml), H2O (20 ml) and CH3COOH (28 ml), was heated at 70° C. for 5.5 h. The solution was evaporated to dryness. The residue was dissolved in water (30 ml), washed with CH2Cl2 and evaporated again. The crude product was purified by flash chromatography on silica gel (chloroform: methanol:30% NH4OH=140:60:6) to yield (S)-(-)-2-amino-4-(2-amino-5-chlorophenyl)-4-oxo butyric acid as yellow crystal (0.29 g; 51.5%; m.p. 206°-208° C.; [α]20D =-12.0° (1%; CH3OOH); ee 96%.

Workup

  1. customThe solution was evaporated to dryness
  2. dissolutionThe residue was dissolved in water (30 ml)
  3. washwashed with CH2Cl2
  4. customevaporated again
  5. customThe crude product was purified by flash chromatography on silica gel (chloroform: methanol:30% NH4OH=140:60:6)

Sources & evidence

ORD record
ord-3154174f442b4c68bb154c695fefa4df
Source dataset
uspto-grants-1998_07
Patent number
US05786508

Reaction notes

Loading…