Hydrochloric Acid → HCID 10891565, compound

HRID 366906Notes

Reaction equation

HRID 366906 reaction equation
CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].[Cl:14][CH2:15][C:16](=[O:31])[C@@H:17]([NH:26][C:27](=[O:30])[O:28][CH3:29])[CH2:18][S:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl>C(O)(C)C>[Cl:14][CH2:15][C@@H:16]([OH:31])[C@@H:17]([NH:26][C:27](=[O:30])[O:28][CH3:29])[CH2:18][S:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11143Aluminum isopropoxideHCID 10869928HCID 10869928, compound

Product 1

HCID 10891565HCID 10891565, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 2.15 g aluminium isopropoxide in 35 ml of isopropanol were added 2.88 g of methyl [3-chloro-2-oxo-(R)-1-(phenylthiomethyl)-propyl]-carbamate and the suspension was stirred at 70° C./ 400 mbar for 4 hours. The mixture was cooled to 0° C., the pH was adjusted to 1 by adding hydrochloric acid and the isopropanol was evaporated. The suspension was filtered and the residue was recrystallized from toluene to give 2.18 g (75%) isomerically pure methyl (1R, 2S)-[3-chloro-2-hydroxy-1-(phenylthiomethyl)-propyl]-carbamate, m.p. 113-114° C. IR (KBr): 3389 m and 3327 m (NH, OH), 1695 s (C=O), 1537 s (amide II). MS (EI): 289/35 (M+).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customthe isopropanol was evaporated
  3. filtrationThe suspension was filtered
  4. customthe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-8762cabee9594213bdc97df827d8cfa4
Source dataset
uspto-grants-2000_10
Patent number
US06130348

Reaction notes

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