Hydrochloric Acid → Benzyl [(2R,3S)-4-chloro-3-hydroxy-1-(phenylsulfanyl)butan-2-yl]carbamate

HRID 366908Notes

Reaction equation

HRID 366908 reaction equation
CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].[Cl:14][CH2:15][C:16](=[O:37])[C@@H:17]([NH:26][C:27](=[O:36])[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[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:37])[C@@H:17]([NH:26][C:27](=[O:36])[O:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[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 10808734Z-D-Phe chloromethyl ketone

Product 1

HCID 9951031Benzyl [(2R,3S)-4-chloro-3-hydroxy-1-(phenylsulfanyl)butan-2-yl]carbamateYield 80%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 2.15 g aluminium isopropoxide in 35 ml of isopropanol were added 3.64 g of benzyl [3-chloro-2-oxo-(R)-1-(phenylthiomethyl)-propyl]-carbamate and the mixture was stirred at 50° 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 residue was partitioned between water and dichloromethane and the organic layer was evaporated. The residue was chromatographed on silica to give 2.9 g (80%) of pure benzyl (1R, 2S)-[3-chloro-2-hydroxy -1-(phenylthiomethyl)-propyl]-carbamate. IR (KBr): 3360 br (NH, OH), 1690 s (C=O), 1540 s (amide II).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customthe isopropanol was evaporated
  3. customThe residue was partitioned between water and dichloromethane
  4. customthe organic layer was evaporated
  5. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-da1f0146ade84064a14ab3983f3b8ee3
Source dataset
uspto-grants-2000_10
Patent number
US06130348

Reaction notes

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